2-{[{2-Hy-droxy-3-[2-methyl-5-(propan-2-yl)phen-oxy]prop-yl}(pyridin-2-ylmeth-yl)amino]-meth-yl}phenol.

In the title racemic compound, C(26)H(32)N(2)O(3), an intra-molecular O-H⋯N hydrogen bond is formed between the phenolic OH group and the tertiary amine N atom. Another O-H⋯N hydrogen bond that is formed between the OH group and the pyridine N atom links the mol-ecules into a polymeric chain extending along the a axis. The structure is further stabilized by intramolecular and intermolecular C-H⋯O interactions.

Related literature

For the synthesis of the title compound, see: Rossi et al. (2005 ▶). For related structures, see: Butcher et al. (2005 ▶, 2007 ▶). For the activities of related metal complexes, see: Ruiz et al. (2010 ▶); Yajima et al. (2002 ▶); Sarkar et al. (2006 ▶); Neves et al. (1999 ▶).

Experimental

Crystal data

C26H32N2O3

M = 420.54

Triclinic,

a = 8.0940 (6) Å

b = 11.3611 (7) Å

c = 13.7625 (10) Å

α = 79.944 (6)°

β = 82.915 (6)°

γ = 71.745 (6)°

V = 1180.21 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.30 × 0.30 × 0.20 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.977, T max = 0.985

23864 measured reflections

4083 independent reflections

3232 reflections with I > 2σ(I)

R int = 0.063

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.163

S = 1.06

4083 reflections

285 parameters

H-atom parameters constrained

Δρmax = 0.99 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020952/gk2373sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020952/gk2373Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020952/gk2373Isup3.cml

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

C26H32N2O3	Z = 2
Mr = 420.54	F(000) = 452
Triclinic, P1	Dx = 1.183 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0940 (6) Å	Cell parameters from 23864 reflections
b = 11.3611 (7) Å	θ = 2.6–25.0°
c = 13.7625 (10) Å	µ = 0.08 mm−1
α = 79.944 (6)°	T = 120 K
β = 82.915 (6)°	Block, colourless
γ = 71.745 (6)°	0.30 × 0.30 × 0.20 mm
V = 1180.21 (15) Å3

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	4083 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3232 reflections with I > 2σ(I)
graphite	Rint = 0.063
ω scans	θmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −9→9
Tmin = 0.977, Tmax = 0.985	k = −13→13
23864 measured reflections	l = −16→16

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0984P)2 + 0.1634P] where P = (Fo2 + 2Fc2)/3
4083 reflections	(Δ/σ)max < 0.001
285 parameters	Δρmax = 0.99 e Å−3
0 restraints	Δρmin = −0.27 e Å−3

Experimental. 1H NMR (p.p.m., CDCl3): 1.20 (d, 6H, 2-CH3), 2.08 (s, 3H, –CH3), 2.84 (d, 2H, –CH2), 3.10 (m, 1H, –CH), 3.90 (m, 4H 2-CH2), 4.10(d, 2H, –CH2), 4.25 (m, 1H, –CH), 4.58 (bs, 1H, Ar—OH), 6.7 to 7.7 Ar—H. (Found: C 74.54, H 7.37, N 6.67%; Calcd. for C26H31O3N2: C 74.44, H 7.44, N 7.05%) IR (cm-l): ? (C═C) 1586, ? (C—O—C) 1151. MS (m/z): 421[M]+

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.7021 (3)	0.58331 (18)	0.23411 (15)	0.0272 (5)
H1	0.6049	0.5897	0.2789	0.033*
C2	0.6851 (3)	0.65628 (19)	0.14101 (15)	0.0289 (5)
C3	0.8326 (3)	0.6470 (2)	0.07647 (15)	0.0308 (5)
H3A	0.8240	0.6956	0.0144	0.037*
C4	0.9931 (3)	0.5658 (2)	0.10358 (16)	0.0317 (5)
H4	1.0904	0.5613	0.0591	0.038*
C5	1.0125 (3)	0.49111 (18)	0.19502 (16)	0.0287 (5)
C6	0.8624 (3)	0.50136 (18)	0.26044 (15)	0.0260 (5)
C7	0.5086 (3)	0.7432 (2)	0.11150 (16)	0.0323 (5)
H7	0.5243	0.7825	0.0431	0.039*
C8	0.4387 (3)	0.8471 (2)	0.17527 (18)	0.0375 (5)
H8A	0.4249	0.8112	0.2432	0.056*
H8B	0.3278	0.9006	0.1540	0.056*
H8C	0.5191	0.8952	0.1689	0.056*
C9	0.3783 (3)	0.6693 (2)	0.11357 (17)	0.0360 (5)
H9A	0.4214	0.6093	0.0683	0.054*
H9B	0.2678	0.7260	0.0945	0.054*
H9C	0.3643	0.6266	0.1792	0.054*
C10	1.1857 (3)	0.4025 (2)	0.22438 (18)	0.0381 (5)
H10A	1.2731	0.4077	0.1712	0.057*
H10B	1.1780	0.3185	0.2383	0.057*
H10C	1.2168	0.4246	0.2823	0.057*
C11	0.7519 (3)	0.43452 (19)	0.42513 (16)	0.0290 (5)
H11A	0.6481	0.4302	0.3992	0.035*
H11B	0.7242	0.5131	0.4511	0.035*
C12	0.8149 (3)	0.32503 (19)	0.50560 (16)	0.0300 (5)
H12	0.8512	0.2478	0.4757	0.036*
C13	0.9716 (3)	0.33436 (18)	0.55172 (15)	0.0249 (4)
H13A	1.0516	0.3589	0.4995	0.030*
H13B	0.9321	0.3992	0.5940	0.030*
C14	0.9973 (3)	0.20672 (18)	0.71470 (14)	0.0253 (4)
H14A	0.8710	0.2386	0.7183	0.030*
H14B	1.0401	0.2583	0.7484	0.030*
C15	1.0514 (2)	0.07363 (18)	0.76661 (14)	0.0247 (4)
C16	1.0327 (3)	−0.02368 (19)	0.72237 (15)	0.0271 (5)
C17	1.0661 (3)	−0.1443 (2)	0.77277 (17)	0.0345 (5)
H17	1.0498	−0.2074	0.7436	0.041*
C18	1.1244 (3)	−0.1707 (2)	0.86749 (17)	0.0392 (6)
H18	1.1463	−0.2515	0.9018	0.047*
C19	1.1499 (3)	−0.0776 (2)	0.91064 (17)	0.0404 (6)
H19	1.1928	−0.0960	0.9729	0.048*
C20	1.1114 (3)	0.0433 (2)	0.86082 (15)	0.0326 (5)
H20	1.1260	0.1061	0.8912	0.039*
C21	1.2544 (2)	0.19811 (18)	0.60307 (14)	0.0239 (4)
H21A	1.3081	0.1279	0.6517	0.029*
H21B	1.2744	0.2722	0.6189	0.029*
C22	1.3400 (2)	0.17410 (17)	0.50250 (14)	0.0227 (4)
C23	1.2875 (3)	0.10394 (18)	0.44568 (15)	0.0273 (5)
H23	1.1955	0.0716	0.4694	0.033*
C24	1.3720 (3)	0.08254 (19)	0.35424 (15)	0.0290 (5)
H24	1.3369	0.0368	0.3153	0.035*
C25	1.5104 (3)	0.13057 (19)	0.32132 (16)	0.0298 (5)
H25	1.5707	0.1177	0.2602	0.036*
C26	1.5555 (3)	0.19783 (19)	0.38222 (15)	0.0296 (5)
H26	1.6486	0.2295	0.3603	0.036*
N1	1.0650 (2)	0.21620 (14)	0.61015 (12)	0.0226 (4)
N2	1.4744 (2)	0.22078 (16)	0.47087 (13)	0.0275 (4)
O1	0.89021 (18)	0.42567 (13)	0.34963 (11)	0.0313 (4)
O2	0.67674 (19)	0.31938 (15)	0.57718 (11)	0.0354 (4)
H2O	0.6056	0.2961	0.5541	0.053*
O3	0.9810 (2)	−0.00092 (14)	0.62858 (11)	0.0341 (4)
H3	0.9930	0.0662	0.6008	0.051*

	U11	U22	U33	U12	U13	U23
C1	0.0266 (11)	0.0251 (10)	0.0336 (11)	−0.0092 (9)	−0.0063 (9)	−0.0082 (9)
C2	0.0310 (11)	0.0274 (11)	0.0339 (11)	−0.0117 (9)	−0.0080 (9)	−0.0095 (9)
C3	0.0360 (12)	0.0321 (11)	0.0292 (11)	−0.0144 (10)	−0.0062 (9)	−0.0069 (9)
C4	0.0331 (12)	0.0330 (12)	0.0339 (12)	−0.0137 (9)	−0.0015 (9)	−0.0118 (9)
C5	0.0284 (11)	0.0240 (11)	0.0388 (12)	−0.0095 (9)	−0.0058 (9)	−0.0130 (9)
C6	0.0299 (11)	0.0211 (10)	0.0311 (11)	−0.0110 (8)	−0.0077 (9)	−0.0046 (8)
C7	0.0294 (12)	0.0343 (12)	0.0348 (12)	−0.0112 (9)	−0.0108 (9)	0.0002 (9)
C8	0.0324 (12)	0.0311 (12)	0.0490 (14)	−0.0083 (10)	−0.0068 (10)	−0.0054 (10)
C9	0.0305 (12)	0.0404 (13)	0.0405 (13)	−0.0115 (10)	−0.0118 (10)	−0.0067 (10)
C10	0.0310 (12)	0.0325 (12)	0.0520 (14)	−0.0095 (10)	−0.0037 (10)	−0.0089 (10)
C11	0.0221 (10)	0.0265 (11)	0.0411 (12)	−0.0101 (8)	−0.0090 (9)	−0.0017 (9)
C12	0.0243 (11)	0.0282 (11)	0.0400 (12)	−0.0124 (9)	−0.0072 (9)	0.0004 (9)
C13	0.0250 (10)	0.0218 (10)	0.0299 (11)	−0.0093 (8)	−0.0039 (8)	−0.0037 (8)
C14	0.0224 (10)	0.0273 (11)	0.0295 (11)	−0.0098 (8)	−0.0028 (8)	−0.0080 (8)
C15	0.0205 (10)	0.0268 (11)	0.0284 (11)	−0.0096 (8)	0.0007 (8)	−0.0051 (8)
C16	0.0210 (10)	0.0309 (11)	0.0324 (11)	−0.0130 (8)	0.0009 (8)	−0.0049 (9)
C17	0.0313 (12)	0.0284 (12)	0.0455 (14)	−0.0137 (9)	0.0033 (10)	−0.0056 (10)
C18	0.0390 (13)	0.0298 (12)	0.0408 (13)	−0.0083 (10)	0.0062 (10)	0.0056 (10)
C19	0.0426 (14)	0.0411 (14)	0.0304 (12)	−0.0066 (11)	−0.0015 (10)	0.0017 (10)
C20	0.0313 (12)	0.0357 (12)	0.0307 (11)	−0.0089 (9)	−0.0001 (9)	−0.0079 (9)
C21	0.0192 (10)	0.0240 (10)	0.0324 (11)	−0.0092 (8)	−0.0057 (8)	−0.0064 (8)
C22	0.0180 (9)	0.0196 (10)	0.0316 (11)	−0.0063 (8)	−0.0064 (8)	−0.0018 (8)
C23	0.0221 (10)	0.0275 (11)	0.0375 (12)	−0.0123 (8)	−0.0034 (9)	−0.0083 (9)
C24	0.0245 (10)	0.0284 (11)	0.0370 (12)	−0.0064 (9)	−0.0058 (9)	−0.0131 (9)
C25	0.0230 (10)	0.0302 (11)	0.0348 (12)	−0.0049 (9)	−0.0009 (9)	−0.0076 (9)
C26	0.0233 (10)	0.0336 (12)	0.0362 (12)	−0.0141 (9)	0.0013 (9)	−0.0080 (9)
N1	0.0183 (8)	0.0230 (8)	0.0288 (9)	−0.0082 (7)	−0.0039 (7)	−0.0042 (7)
N2	0.0230 (9)	0.0280 (9)	0.0362 (10)	−0.0127 (7)	−0.0032 (7)	−0.0073 (7)
O1	0.0266 (8)	0.0294 (8)	0.0365 (8)	−0.0063 (6)	−0.0073 (6)	−0.0015 (6)
O2	0.0309 (9)	0.0410 (9)	0.0389 (9)	−0.0168 (7)	−0.0047 (7)	−0.0051 (7)
O3	0.0400 (9)	0.0315 (8)	0.0405 (9)	−0.0206 (7)	−0.0123 (7)	−0.0054 (7)

C1—C6	1.386 (3)	C13—H13B	0.9700
C1—C2	1.396 (3)	C14—N1	1.473 (3)
C1—H1	0.9300	C14—C15	1.508 (3)
C2—C3	1.384 (3)	C14—H14A	0.9700
C2—C7	1.516 (3)	C14—H14B	0.9700
C3—C4	1.388 (3)	C15—C20	1.389 (3)
C3—H3A	0.9300	C15—C16	1.407 (3)
C4—C5	1.386 (3)	C16—O3	1.362 (2)
C4—H4	0.9300	C16—C17	1.384 (3)
C5—C6	1.406 (3)	C17—C18	1.392 (3)
C5—C10	1.502 (3)	C17—H17	0.9300
C6—O1	1.369 (2)	C18—C19	1.378 (3)
C7—C8	1.518 (3)	C18—H18	0.9300
C7—C9	1.535 (3)	C19—C20	1.382 (3)
C7—H7	0.9800	C19—H19	0.9300
C8—H8A	0.9600	C20—H20	0.9300
C8—H8B	0.9600	C21—N1	1.474 (2)
C8—H8C	0.9600	C21—C22	1.499 (3)
C9—H9A	0.9600	C21—H21A	0.9700
C9—H9B	0.9600	C21—H21B	0.9700
C9—H9C	0.9600	C22—N2	1.348 (3)
C10—H10A	0.9600	C22—C23	1.393 (3)
C10—H10B	0.9600	C23—C24	1.379 (3)
C10—H10C	0.9600	C23—H23	0.9300
C11—O1	1.422 (3)	C24—C25	1.389 (3)
C11—C12	1.515 (3)	C24—H24	0.9300
C11—H11A	0.9700	C25—C26	1.376 (3)
C11—H11B	0.9700	C25—H25	0.9300
C12—O2	1.406 (3)	C26—N2	1.339 (3)
C12—C13	1.526 (3)	C26—H26	0.9300
C12—H12	0.9800	O2—H2O	0.8200
C13—N1	1.469 (2)	O3—H3	0.8200
C13—H13A	0.9700
C6—C1—C2	120.7 (2)	C12—C13—H13A	109.0
C6—C1—H1	119.7	N1—C13—H13B	109.0
C2—C1—H1	119.7	C12—C13—H13B	109.0
C3—C2—C1	118.5 (2)	H13A—C13—H13B	107.8
C3—C2—C7	120.99 (19)	N1—C14—C15	111.99 (16)
C1—C2—C7	120.52 (19)	N1—C14—H14A	109.2
C2—C3—C4	120.6 (2)	C15—C14—H14A	109.2
C2—C3—H3A	119.7	N1—C14—H14B	109.2
C4—C3—H3A	119.7	C15—C14—H14B	109.2
C5—C4—C3	121.9 (2)	H14A—C14—H14B	107.9
C5—C4—H4	119.1	C20—C15—C16	117.71 (18)
C3—C4—H4	119.1	C20—C15—C14	121.98 (18)
C4—C5—C6	117.28 (19)	C16—C15—C14	120.21 (17)
C4—C5—C10	122.1 (2)	O3—C16—C17	118.51 (19)
C6—C5—C10	120.66 (19)	O3—C16—C15	120.51 (18)
O1—C6—C1	124.48 (19)	C17—C16—C15	120.97 (19)
O1—C6—C5	114.48 (18)	C16—C17—C18	119.5 (2)
C1—C6—C5	121.04 (19)	C16—C17—H17	120.2
C2—C7—C8	111.83 (17)	C18—C17—H17	120.2
C2—C7—C9	110.83 (17)	C19—C18—C17	120.3 (2)
C8—C7—C9	111.36 (19)	C19—C18—H18	119.8
C2—C7—H7	107.5	C17—C18—H18	119.8
C8—C7—H7	107.5	C18—C19—C20	119.7 (2)
C9—C7—H7	107.5	C18—C19—H19	120.2
C7—C8—H8A	109.5	C20—C19—H19	120.2
C7—C8—H8B	109.5	C19—C20—C15	121.7 (2)
H8A—C8—H8B	109.5	C19—C20—H20	119.1
C7—C8—H8C	109.5	C15—C20—H20	119.1
H8A—C8—H8C	109.5	N1—C21—C22	112.97 (15)
H8B—C8—H8C	109.5	N1—C21—H21A	109.0
C7—C9—H9A	109.5	C22—C21—H21A	109.0
C7—C9—H9B	109.5	N1—C21—H21B	109.0
H9A—C9—H9B	109.5	C22—C21—H21B	109.0
C7—C9—H9C	109.5	H21A—C21—H21B	107.8
H9A—C9—H9C	109.5	N2—C22—C23	121.50 (19)
H9B—C9—H9C	109.5	N2—C22—C21	116.56 (16)
C5—C10—H10A	109.5	C23—C22—C21	121.91 (17)
C5—C10—H10B	109.5	C24—C23—C22	119.90 (19)
H10A—C10—H10B	109.5	C24—C23—H23	120.1
C5—C10—H10C	109.5	C22—C23—H23	120.1
H10A—C10—H10C	109.5	C23—C24—C25	118.79 (19)
H10B—C10—H10C	109.5	C23—C24—H24	120.6
O1—C11—C12	106.52 (16)	C25—C24—H24	120.6
O1—C11—H11A	110.4	C26—C25—C24	117.8 (2)
C12—C11—H11A	110.4	C26—C25—H25	121.1
O1—C11—H11B	110.4	C24—C25—H25	121.1
C12—C11—H11B	110.4	N2—C26—C25	124.49 (19)
H11A—C11—H11B	108.6	N2—C26—H26	117.8
O2—C12—C11	109.42 (16)	C25—C26—H26	117.8
O2—C12—C13	111.46 (17)	C13—N1—C14	112.26 (15)
C11—C12—C13	111.23 (16)	C13—N1—C21	111.67 (15)
O2—C12—H12	108.2	C14—N1—C21	110.08 (15)
C11—C12—H12	108.2	C26—N2—C22	117.52 (17)
C13—C12—H12	108.2	C6—O1—C11	119.89 (15)
N1—C13—C12	112.82 (15)	C12—O2—H2O	109.5
N1—C13—H13A	109.0	C16—O3—H3	109.5
C6—C1—C2—C3	−1.4 (3)	O3—C16—C17—C18	177.95 (19)
C6—C1—C2—C7	178.34 (17)	C15—C16—C17—C18	−2.0 (3)
C1—C2—C3—C4	0.7 (3)	C16—C17—C18—C19	−0.5 (3)
C7—C2—C3—C4	−179.02 (18)	C17—C18—C19—C20	2.3 (3)
C2—C3—C4—C5	0.2 (3)	C18—C19—C20—C15	−1.7 (3)
C3—C4—C5—C6	−0.5 (3)	C16—C15—C20—C19	−0.7 (3)
C3—C4—C5—C10	179.60 (18)	C14—C15—C20—C19	175.7 (2)
C2—C1—C6—O1	−179.35 (17)	N1—C21—C22—N2	145.52 (17)
C2—C1—C6—C5	1.2 (3)	N1—C21—C22—C23	−36.4 (2)
C4—C5—C6—O1	−179.73 (17)	N2—C22—C23—C24	−1.0 (3)
C10—C5—C6—O1	0.2 (3)	C21—C22—C23—C24	−178.94 (18)
C4—C5—C6—C1	−0.2 (3)	C22—C23—C24—C25	0.9 (3)
C10—C5—C6—C1	179.71 (18)	C23—C24—C25—C26	−0.2 (3)
C3—C2—C7—C8	−115.7 (2)	C24—C25—C26—N2	−0.4 (3)
C1—C2—C7—C8	64.5 (3)	C12—C13—N1—C14	−90.37 (19)
C3—C2—C7—C9	119.4 (2)	C12—C13—N1—C21	145.45 (17)
C1—C2—C7—C9	−60.4 (3)	C15—C14—N1—C13	162.17 (15)
O1—C11—C12—O2	−172.92 (15)	C15—C14—N1—C21	−72.78 (19)
O1—C11—C12—C13	63.5 (2)	C22—C21—N1—C13	−69.2 (2)
O2—C12—C13—N1	72.9 (2)	C22—C21—N1—C14	165.45 (15)
C11—C12—C13—N1	−164.73 (17)	C25—C26—N2—C22	0.3 (3)
N1—C14—C15—C20	136.15 (19)	C23—C22—N2—C26	0.4 (3)
N1—C14—C15—C16	−47.5 (2)	C21—C22—N2—C26	178.44 (17)
C20—C15—C16—O3	−177.38 (18)	C1—C6—O1—C11	−4.5 (3)
C14—C15—C16—O3	6.1 (3)	C5—C6—O1—C11	175.02 (16)
C20—C15—C16—C17	2.6 (3)	C12—C11—O1—C6	170.36 (15)
C14—C15—C16—C17	−173.90 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N2i	0.82	2.09	2.897 (2)	166
O3—H3···N1	0.82	1.99	2.721 (2)	147
C14—H14A···O2	0.97	2.51	3.199 (3)	128
C23—H23···O3ii	0.93	2.47	3.114 (3)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯N2i	0.82	2.09	2.897 (2)	166
O3—H3⋯N1	0.82	1.99	2.721 (2)	147
C14—H14A⋯O2	0.97	2.51	3.199 (3)	128
C23—H23⋯O3ii	0.93	2.47	3.114 (3)	127

Symmetry codes: (i) ; (ii) .