(E)-3-(8-Benz-yloxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1-[2-hy-droxy-4,6-bis-(meth-oxy-meth-oxy)phen-yl]prop-2-en-1-one.

In the title mol-ecule, C(28)H(28)O(9), the phenol and the benzene rings adjacent to the α,β-unsaturated ketone unit are inclined at 9.15 (13)° to each other. The terminal phenyl ring is oriented with respect to the phenol ring at a dihedral angle of 85.88 (13)°. In the crystal, the methyl-ene C atoms of the dihydro-dioxine ring are disordered over two sites with an occupancy ratio of 0.463 (18):0.537 (18), and both disordered components of the dihydro-dioxine ring adopt twisted-chair conformations. An intra-molecular O-H⋯O hydrogen bond and weak inter-molecular C-H⋯O hydrogen bonds are present in the crystal structure.

Related literature

For background to 1,3-diaryl-2-propen-1-one, see: Carlo et al. (1999 ▶); Dimmock et al. (1999 ▶); Go et al. (2005 ▶); Nowakowska (2007 ▶); Yarishkin et al. (2008 ▶). For related structures, see: Özbey et al. (1997 ▶); Gao & Ng (2006 ▶); Loghmani-Khouzani et al. (2009 ▶); Rizvi et al. (2010 ▶). For the synthesis, see: Lin et al. (2007 ▶).

Experimental

Crystal data

C28H28O9

M = 508.50

Triclinic,

a = 8.149 (4) Å

b = 11.744 (5) Å

c = 14.439 (7) Å

α = 72.752 (5)°

β = 84.269 (5)°

γ = 70.601 (5)°

V = 1244.7 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 294 K

0.35 × 0.25 × 0.18 mm

Data collection

Bruker CCD 1000 area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.965, T max = 0.982

5687 measured reflections

4774 independent reflections

3239 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.195

S = 1.02

4774 reflections

353 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100924X/xu5171sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100924X/xu5171Isup2.hkl

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

C28H28O9	Z = 2
Mr = 508.50	F(000) = 536
Triclinic, P1	Dx = 1.357 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.149 (4) Å	Cell parameters from 847 reflections
b = 11.744 (5) Å	θ = 2.7–27.1°
c = 14.439 (7) Å	µ = 0.10 mm−1
α = 72.752 (5)°	T = 294 K
β = 84.269 (5)°	Block, orange
γ = 70.601 (5)°	0.35 × 0.25 × 0.18 mm
V = 1244.7 (10) Å3

Bruker CCD 1000 area-detector diffractometer	4774 independent reflections
Radiation source: sealed tube	3239 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
Tmin = 0.965, Tmax = 0.982	k = −14→12
5687 measured reflections	l = −17→17

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.126P)2] where P = (Fo2 + 2Fc2)/3
4774 reflections	(Δ/σ)max < 0.001
353 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.21 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	Occ. (<1)
O1	−0.02313 (19)	0.61404 (14)	0.91280 (12)	0.0582 (5)
O2	−0.2521 (2)	0.86192 (14)	0.83479 (12)	0.0597 (5)
O3	0.29103 (19)	0.54252 (13)	0.84269 (11)	0.0558 (5)
O4	0.3240 (2)	1.09630 (15)	0.44508 (13)	0.0642 (5)
O5	−0.1587 (2)	1.65623 (15)	0.28563 (12)	0.0647 (5)
O6	−0.2044 (3)	1.83191 (15)	0.15912 (13)	0.0736 (5)
O7	−0.1328 (2)	1.30029 (15)	0.55058 (12)	0.0659 (5)
O8	−0.4304 (3)	1.35542 (18)	0.53966 (16)	0.0848 (6)
O9	0.3228 (2)	1.28722 (16)	0.31656 (13)	0.0668 (5)
H9C	0.3572	1.2137	0.3494	0.100*
C1	−0.172 (2)	0.6699 (16)	0.9639 (10)	0.086 (4)	0.463 (18)
H1A	−0.2494	0.6200	0.9719	0.103*	0.463 (18)
H1B	−0.1333	0.6586	1.0283	0.103*	0.463 (18)
C2	−0.2644 (15)	0.7837 (9)	0.9331 (7)	0.057 (2)	0.463 (18)
H2A	−0.2440	0.8268	0.9765	0.069*	0.463 (18)
H2B	−0.3847	0.7855	0.9424	0.069*	0.463 (18)
C1'	−0.2038 (13)	0.6528 (9)	0.9316 (8)	0.054 (2)	0.537 (18)
H1'1	−0.2492	0.5982	0.9103	0.065*	0.537 (18)
H1'2	−0.2150	0.6304	1.0017	0.065*	0.537 (18)
C2'	−0.3120 (14)	0.7637 (13)	0.9008 (13)	0.110 (5)	0.537 (18)
H2'1	−0.3615	0.7923	0.9570	0.132*	0.537 (18)
H2'2	−0.4062	0.7567	0.8690	0.132*	0.537 (18)
C3	−0.0883 (3)	0.82076 (19)	0.79882 (16)	0.0448 (5)
C4	0.0230 (3)	0.69963 (18)	0.83660 (15)	0.0443 (5)
C5	0.1907 (3)	0.66401 (18)	0.79889 (16)	0.0451 (5)
C6	0.2440 (3)	0.74792 (19)	0.72391 (16)	0.0474 (5)
H6A	0.3559	0.7236	0.6991	0.057*
C7	0.1314 (3)	0.86943 (18)	0.68465 (15)	0.0432 (5)
C8	−0.0349 (3)	0.90484 (19)	0.72278 (16)	0.0458 (5)
H8A	−0.1109	0.9854	0.6971	0.055*
C9	0.4658 (3)	0.5063 (2)	0.8107 (2)	0.0668 (7)
H9A	0.5240	0.5615	0.8209	0.080*
H9B	0.4686	0.5137	0.7419	0.080*
C10	0.5581 (3)	0.3732 (2)	0.86577 (16)	0.0493 (6)
C11	0.5419 (3)	0.2761 (2)	0.83868 (17)	0.0581 (6)
H11A	0.4675	0.2931	0.7880	0.070*
C12	0.6339 (4)	0.1524 (2)	0.8848 (2)	0.0697 (7)
H12A	0.6209	0.0874	0.8651	0.084*
C13	0.7425 (4)	0.1264 (2)	0.9585 (2)	0.0699 (8)
H13A	0.8061	0.0434	0.9885	0.084*
C14	0.7594 (4)	0.2206 (3)	0.9891 (2)	0.0758 (8)
H14A	0.8328	0.2021	1.0406	0.091*
C15	0.6664 (3)	0.3454 (2)	0.9430 (2)	0.0663 (7)
H15A	0.6772	0.4100	0.9642	0.080*
C16	0.1943 (3)	0.95607 (19)	0.60541 (15)	0.0453 (5)
H16A	0.3115	0.9287	0.5893	0.054*
C17	0.1011 (3)	1.06911 (19)	0.55476 (16)	0.0478 (5)
H17A	−0.0167	1.0994	0.5686	0.057*
C18	0.1795 (3)	1.1487 (2)	0.47661 (16)	0.0458 (5)
C19	0.0915 (3)	1.28298 (19)	0.43388 (15)	0.0431 (5)
C20	−0.0676 (3)	1.35676 (19)	0.46461 (15)	0.0461 (5)
C21	−0.1479 (3)	1.4795 (2)	0.41326 (16)	0.0510 (6)
H21A	−0.2552	1.5247	0.4335	0.061*
C22	−0.0687 (3)	1.53574 (19)	0.33120 (16)	0.0487 (5)
C23	0.0905 (3)	1.4708 (2)	0.30072 (16)	0.0528 (6)
H23A	0.1448	1.5100	0.2470	0.063*
C24	0.1693 (3)	1.3463 (2)	0.35090 (15)	0.0473 (5)
C25	−0.0851 (4)	1.7180 (3)	0.19855 (19)	0.0734 (8)
H25A	0.0211	1.7290	0.2134	0.088*
H25B	−0.0575	1.6677	0.1531	0.088*
C26	−0.2259 (6)	1.9197 (3)	0.2108 (3)	0.1194 (14)
H26A	−0.3122	1.9971	0.1795	0.179*
H26B	−0.1174	1.9344	0.2126	0.179*
H26C	−0.2627	1.8876	0.2758	0.179*
C27	−0.2982 (3)	1.3618 (2)	0.5841 (2)	0.0680 (7)
H27A	−0.3059	1.3242	0.6533	0.082*
H27B	−0.3094	1.4495	0.5740	0.082*
C28	−0.4456 (5)	1.2299 (3)	0.5652 (3)	0.0982 (11)
H28A	−0.5417	1.2315	0.5308	0.147*
H28B	−0.4649	1.2023	0.6337	0.147*
H28C	−0.3402	1.1729	0.5478	0.147*

	U11	U22	U33	U12	U13	U23
O1	0.0523 (10)	0.0408 (9)	0.0614 (10)	−0.0101 (7)	0.0183 (7)	0.0037 (7)
O2	0.0496 (9)	0.0402 (9)	0.0694 (11)	−0.0047 (7)	0.0203 (8)	−0.0036 (7)
O3	0.0429 (9)	0.0350 (8)	0.0643 (10)	−0.0012 (6)	0.0149 (7)	0.0053 (7)
O4	0.0442 (9)	0.0503 (10)	0.0700 (11)	−0.0021 (7)	0.0110 (8)	0.0056 (8)
O5	0.0641 (11)	0.0434 (9)	0.0637 (11)	−0.0075 (8)	0.0032 (8)	0.0065 (8)
O6	0.0993 (15)	0.0432 (10)	0.0642 (11)	−0.0155 (9)	−0.0202 (10)	0.0038 (8)
O7	0.0589 (10)	0.0522 (10)	0.0613 (10)	−0.0085 (8)	0.0240 (8)	0.0028 (8)
O8	0.0620 (12)	0.0685 (13)	0.1118 (17)	−0.0101 (10)	0.0126 (11)	−0.0240 (12)
O9	0.0468 (10)	0.0562 (10)	0.0720 (11)	−0.0076 (8)	0.0192 (8)	0.0028 (8)
C1	0.064 (7)	0.089 (8)	0.065 (7)	−0.001 (5)	0.024 (5)	0.003 (5)
C2	0.043 (5)	0.047 (4)	0.061 (5)	−0.006 (3)	0.025 (3)	−0.003 (3)
C1'	0.042 (3)	0.043 (3)	0.060 (5)	−0.013 (2)	0.016 (4)	0.007 (3)
C2'	0.053 (5)	0.092 (7)	0.125 (10)	−0.012 (4)	0.027 (5)	0.036 (7)
C3	0.0383 (11)	0.0347 (11)	0.0536 (13)	−0.0068 (9)	0.0085 (9)	−0.0094 (9)
C4	0.0463 (12)	0.0347 (11)	0.0464 (12)	−0.0138 (9)	0.0078 (9)	−0.0051 (9)
C5	0.0432 (12)	0.0310 (10)	0.0515 (13)	−0.0066 (9)	0.0063 (9)	−0.0054 (9)
C6	0.0399 (11)	0.0366 (11)	0.0544 (13)	−0.0068 (9)	0.0099 (9)	−0.0056 (9)
C7	0.0433 (12)	0.0352 (11)	0.0464 (12)	−0.0114 (9)	0.0033 (9)	−0.0067 (9)
C8	0.0437 (12)	0.0295 (10)	0.0533 (13)	−0.0056 (9)	0.0052 (9)	−0.0041 (9)
C9	0.0472 (14)	0.0437 (13)	0.0808 (18)	−0.0031 (11)	0.0211 (12)	0.0047 (12)
C10	0.0377 (11)	0.0393 (12)	0.0558 (14)	−0.0047 (9)	0.0124 (10)	−0.0038 (10)
C11	0.0586 (15)	0.0560 (15)	0.0532 (14)	−0.0139 (12)	0.0013 (11)	−0.0113 (11)
C12	0.083 (2)	0.0442 (14)	0.0769 (18)	−0.0134 (13)	0.0072 (15)	−0.0205 (13)
C13	0.0599 (16)	0.0448 (14)	0.0790 (19)	0.0017 (12)	0.0042 (14)	−0.0014 (13)
C14	0.0631 (18)	0.077 (2)	0.0727 (18)	−0.0190 (15)	−0.0193 (14)	0.0036 (15)
C15	0.0725 (18)	0.0574 (16)	0.0744 (18)	−0.0275 (13)	0.0030 (14)	−0.0194 (13)
C16	0.0419 (12)	0.0372 (11)	0.0493 (13)	−0.0102 (9)	0.0057 (9)	−0.0056 (9)
C17	0.0381 (11)	0.0385 (11)	0.0556 (13)	−0.0096 (9)	0.0052 (9)	−0.0011 (10)
C18	0.0373 (11)	0.0435 (12)	0.0479 (12)	−0.0107 (9)	0.0007 (9)	−0.0031 (9)
C19	0.0356 (11)	0.0407 (11)	0.0451 (12)	−0.0105 (9)	0.0012 (9)	−0.0030 (9)
C20	0.0430 (12)	0.0420 (12)	0.0461 (12)	−0.0138 (9)	0.0065 (9)	−0.0037 (9)
C21	0.0439 (12)	0.0424 (12)	0.0542 (14)	−0.0050 (10)	0.0072 (10)	−0.0074 (10)
C22	0.0504 (13)	0.0365 (11)	0.0495 (13)	−0.0112 (10)	−0.0042 (10)	0.0003 (9)
C23	0.0500 (13)	0.0469 (13)	0.0483 (13)	−0.0153 (11)	0.0071 (10)	0.0035 (10)
C24	0.0389 (12)	0.0475 (13)	0.0492 (13)	−0.0153 (10)	0.0058 (9)	−0.0047 (10)
C25	0.0837 (19)	0.0560 (16)	0.0585 (16)	−0.0155 (14)	−0.0043 (13)	0.0096 (12)
C26	0.211 (5)	0.061 (2)	0.090 (2)	−0.051 (2)	−0.006 (3)	−0.0159 (18)
C27	0.0657 (18)	0.0594 (16)	0.0700 (17)	−0.0178 (13)	0.0291 (14)	−0.0172 (13)
C28	0.090 (2)	0.082 (2)	0.130 (3)	−0.0292 (18)	0.019 (2)	−0.044 (2)

O1—C4	1.369 (2)	C9—C10	1.497 (3)
O1—C1'	1.413 (10)	C9—H9A	0.9700
O1—C1	1.425 (14)	C9—H9B	0.9700
O2—C3	1.366 (2)	C10—C11	1.358 (3)
O2—C2'	1.452 (11)	C10—C15	1.384 (3)
O2—C2	1.458 (10)	C11—C12	1.385 (3)
O3—C5	1.377 (2)	C11—H11A	0.9300
O3—C9	1.416 (3)	C12—C13	1.350 (4)
O4—C18	1.245 (2)	C12—H12A	0.9300
O5—C22	1.352 (3)	C13—C14	1.357 (4)
O5—C25	1.437 (3)	C13—H13A	0.9300
O6—C25	1.362 (3)	C14—C15	1.396 (4)
O6—C26	1.400 (4)	C14—H14A	0.9300
O7—C20	1.370 (2)	C15—H15A	0.9300
O7—C27	1.415 (3)	C16—C17	1.319 (3)
O8—C27	1.341 (3)	C16—H16A	0.9300
O8—C28	1.455 (4)	C17—C18	1.477 (3)
O9—C24	1.340 (2)	C17—H17A	0.9300
O9—H9C	0.8200	C18—C19	1.464 (3)
C1—C2	1.264 (19)	C19—C20	1.413 (3)
C1—H1A	0.9700	C19—C24	1.422 (3)
C1—H1B	0.9700	C20—C21	1.375 (3)
C2—H2A	0.9700	C21—C22	1.387 (3)
C2—H2B	0.9700	C21—H21A	0.9300
C1'—C2'	1.282 (15)	C22—C23	1.373 (3)
C1'—H1'1	0.9700	C23—C24	1.384 (3)
C1'—H1'2	0.9700	C23—H23A	0.9300
C2'—H2'1	0.9700	C25—H25A	0.9700
C2'—H2'2	0.9700	C25—H25B	0.9700
C3—C8	1.384 (3)	C26—H26A	0.9600
C3—C4	1.388 (3)	C26—H26B	0.9600
C4—C5	1.395 (3)	C26—H26C	0.9600
C5—C6	1.374 (3)	C27—H27A	0.9700
C6—C7	1.398 (3)	C27—H27B	0.9700
C6—H6A	0.9300	C28—H28A	0.9600
C7—C8	1.388 (3)	C28—H28B	0.9600
C7—C16	1.465 (3)	C28—H28C	0.9600
C8—H8A	0.9300
C4—O1—C1'	112.0 (4)	C12—C11—H11A	119.3
C4—O1—C1	113.1 (6)	C13—C12—C11	119.9 (2)
C1'—O1—C1	26.9 (7)	C13—C12—H12A	120.0
C3—O2—C2'	114.7 (5)	C11—C12—H12A	120.0
C3—O2—C2	110.1 (5)	C12—C13—C14	120.4 (3)
C2'—O2—C2	30.5 (7)	C12—C13—H13A	119.8
C5—O3—C9	116.05 (16)	C14—C13—H13A	119.8
C22—O5—C25	117.68 (19)	C13—C14—C15	119.8 (3)
C25—O6—C26	113.9 (3)	C13—C14—H14A	120.1
C20—O7—C27	120.56 (18)	C15—C14—H14A	120.1
C27—O8—C28	113.5 (2)	C10—C15—C14	120.2 (2)
C24—O9—H9C	109.5	C10—C15—H15A	119.9
C2—C1—O1	122.3 (10)	C14—C15—H15A	119.9
C2—C1—H1A	106.8	C17—C16—C7	126.4 (2)
O1—C1—H1A	106.8	C17—C16—H16A	116.8
C2—C1—H1B	106.8	C7—C16—H16A	116.8
O1—C1—H1B	106.8	C16—C17—C18	121.5 (2)
H1A—C1—H1B	106.6	C16—C17—H17A	119.2
C1—C2—O2	123.6 (9)	C18—C17—H17A	119.2
C1—C2—H2A	106.4	O4—C18—C19	119.96 (18)
O2—C2—H2A	106.4	O4—C18—C17	117.31 (19)
C1—C2—H2B	106.4	C19—C18—C17	122.70 (18)
O2—C2—H2B	106.4	C20—C19—C24	115.78 (19)
H2A—C2—H2B	106.5	C20—C19—C18	126.62 (18)
C2'—C1'—O1	126.8 (8)	C24—C19—C18	117.56 (18)
C2'—C1'—H1'1	105.6	O7—C20—C21	122.18 (19)
O1—C1'—H1'1	105.6	O7—C20—C19	115.90 (18)
C2'—C1'—H1'2	105.6	C21—C20—C19	121.86 (19)
O1—C1'—H1'2	105.6	C20—C21—C22	119.9 (2)
H1'1—C1'—H1'2	106.1	C20—C21—H21A	120.0
C1'—C2'—O2	119.3 (8)	C22—C21—H21A	120.0
C1'—C2'—H2'1	107.5	O5—C22—C23	123.9 (2)
O2—C2'—H2'1	107.5	O5—C22—C21	115.3 (2)
C1'—C2'—H2'2	107.5	C23—C22—C21	120.8 (2)
O2—C2'—H2'2	107.5	C22—C23—C24	119.27 (19)
H2'1—C2'—H2'2	107.0	C22—C23—H23A	120.4
O2—C3—C8	117.66 (18)	C24—C23—H23A	120.4
O2—C3—C4	122.02 (18)	O9—C24—C23	116.51 (18)
C8—C3—C4	120.32 (18)	O9—C24—C19	121.29 (19)
O1—C4—C3	122.35 (18)	C23—C24—C19	122.19 (19)
O1—C4—C5	118.11 (18)	O6—C25—O5	107.9 (2)
C3—C4—C5	119.49 (18)	O6—C25—H25A	110.1
C6—C5—O3	125.25 (18)	O5—C25—H25A	110.1
C6—C5—C4	120.08 (19)	O6—C25—H25B	110.1
O3—C5—C4	114.67 (17)	O5—C25—H25B	110.1
C5—C6—C7	120.63 (19)	H25A—C25—H25B	108.4
C5—C6—H6A	119.7	O6—C26—H26A	109.5
C7—C6—H6A	119.7	O6—C26—H26B	109.5
C8—C7—C6	119.15 (18)	H26A—C26—H26B	109.5
C8—C7—C16	122.12 (19)	O6—C26—H26C	109.5
C6—C7—C16	118.73 (19)	H26A—C26—H26C	109.5
C3—C8—C7	120.32 (19)	H26B—C26—H26C	109.5
C3—C8—H8A	119.8	O8—C27—O7	113.2 (2)
C7—C8—H8A	119.8	O8—C27—H27A	108.9
O3—C9—C10	109.76 (17)	O7—C27—H27A	108.9
O3—C9—H9A	109.7	O8—C27—H27B	108.9
C10—C9—H9A	109.7	O7—C27—H27B	108.9
O3—C9—H9B	109.7	H27A—C27—H27B	107.8
C10—C9—H9B	109.7	O8—C28—H28A	109.5
H9A—C9—H9B	108.2	O8—C28—H28B	109.5
C11—C10—C15	118.2 (2)	H28A—C28—H28B	109.5
C11—C10—C9	120.4 (2)	O8—C28—H28C	109.5
C15—C10—C9	121.4 (2)	H28A—C28—H28C	109.5
C10—C11—C12	121.4 (3)	H28B—C28—H28C	109.5
C10—C11—H11A	119.3

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9C···O4	0.82	1.71	2.448 (2)	149
C6—H6A···O9i	0.93	2.57	3.426 (3)	154
C21—H21A···O8ii	0.93	2.53	3.453 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O9—H9C⋯O4	0.82	1.71	2.448 (2)	149
C6—H6A⋯O9i	0.93	2.57	3.426 (3)	154
C21—H21A⋯O8ii	0.93	2.53	3.453 (3)	169

Symmetry codes: (i) ; (ii) .