1-[3-(2-Benz-yloxy-6-hy-droxy-4-methyl-phen-yl)-5-[3,5-bis-(tri-fluoro-meth-yl)phen-yl]-4,5-di-hydro-1H-pyrazol-1-yl]propane-1-one.

In the title compound, C28H24F6N2O3, the mean plane of the central pyrazoline ring forms dihedral angles of 2.08 (9) and 69.02 (16)° with the 2-benz-yloxy-6-hy-droxy-4-methyl-phenyl and 3,5-bis-(tri-fluoro-meth-yl)phenyl rings, respectively. The dihedral angle between the mean planes of the pyrazoline and 3,5-bis-(tri-fluoro-meth-yl)phenyl rings is 68.97 (9)°. An intra-molecular O-H⋯N hydrogen bond is observed, which forms an S(6) graph-set motif. In the crystal, pairs of weak C-H⋯F halogen inter-actions link the mol-ecules into inversion dimers while molecular chains along [100] are formed by C-H⋯O contacts.

Related literature

For pharmacalogical and anti­cancer properties of pyrazoline derivatives, see: Smith et al. (2001 ▶). For graph-set motifs, see: Bernstein et al., (1995 ▶). For related structures, see: Patel et al. (2007 ▶, 2012 ▶).

Experimental

Crystal data

C28H24F6N2O3

M = 550.49

Monoclinic,

a = 4.8822 (2) Å

b = 23.4752 (9) Å

c = 22.4311 (9) Å

β = 91.494 (2)°

V = 2569.97 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 273 K

0.54 × 0.34 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.951, T max = 0.988

19610 measured reflections

4514 independent reflections

2491 reflections with I > 2σ(I)

R int = 0.075

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.246

S = 1.00

4514 reflections

352 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.41 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶ ); cell refinement: SAINT (Bruker, 2008 ▶ ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681301180X/jj2162sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301180X/jj2162Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301180X/jj2162Isup3.cml

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

C28H24F6N2O3	Z = 4
Mr = 550.49	F(000) = 1136
Monoclinic, P21/n	Dx = 1.423 Mg m−3
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 4.8822 (2) Å	θ = 2.9–27.7°
b = 23.4752 (9) Å	µ = 0.12 mm−1
c = 22.4311 (9) Å	T = 273 K
β = 91.494 (2)°	Needle, white
V = 2569.97 (18) Å3	0.54 × 0.34 × 0.10 mm

Bruker Kappa APEXII CCD diffractometer	4514 independent reflections
Radiation source: sealed X-ray tube	2491 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
CCD scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −5→5
Tmin = 0.951, Tmax = 0.988	k = −27→27
19610 measured reflections	l = −26→26

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.246	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1524P)2] where P = (Fo2 + 2Fc2)/3
4514 reflections	(Δ/σ)max < 0.001
352 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

Experimental. IR (cm-1): 2929 (C—H str. (asym) alkyl), 1458 (C—H def (asym)alkyl), 1387(C—H def (sym) alkyl), 3072 (C—H str.arom.), 1593. (C=Cstr. arom.), 1128 (C—H i.p.def arom.), 847 (C—H o.o.p.def.arom.), 1272 (C—O—C (sym) ether), 1066 (C—O—C (asym) ether), 3380(OHstr. phenol). 1659 (N—CO¬ CH2CH3), 1379 (N-COCH2CH3 def., pyrazoline), 1588 (C=N str., pyrazoline), 2863 (C—H ring (str.), pyrazoline), 682 (C—H def. of CH2, pyrazoline), 1197 (C—N str., pyrazoline), 1117 (C—F str.).1H NMR (CDCl3) δp.p.m.: 0.96 (trip, 3H, J=7.3 &7.2 Hz), 1.70 (Qur, 2H),2.31(s,3H), 3.36 (dd, 1H, J=15.3 & 3.5 Hz), 3.83 (dd, 1H, J=11.7 & 7.2 Hz), 5.02 (s, 2H), 5.32 (trip, 1H, J= 3.1 & 8.08 Hz), 6.33 (S, 1H), 6.52 (S,1H), 7.16–7.23(m, 8H), 11.24 (s, 1H).13C NMR (CDCl3) δp.p.m.: 21.98(C-1, CH3), 70.91 (C-2,CH2 C6 H5), 159.37(C-3,Pyrazoline), 46.49 (C-4,Pyrazoline), 57.92 (C-5, Pyrazoline), 170.03(C-6,CO CH2 CH3), 36.15 (C-7,CO CH2 CH3), 13.83 (C-8, CO CH2 CH3), 124.44(C-9, CF3), 124.44 (C-10, CF3).

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
N1	0.1214 (5)	0.55900 (10)	0.66924 (11)	0.0539 (7)
N2	0.3088 (5)	0.58603 (11)	0.63303 (10)	0.0543 (7)
C3	0.3815 (6)	0.63423 (12)	0.65664 (13)	0.0496 (8)
C4	0.2432 (7)	0.64580 (13)	0.71404 (14)	0.0579 (8)
H4A	0.135	0.6804	0.7115	0.069*
H4B	0.3757	0.6492	0.7468	0.069*
C5	0.0589 (6)	0.59313 (13)	0.72178 (13)	0.0515 (8)
H5	−0.1338	0.6048	0.7195	0.062*
C6	−0.0355 (7)	0.51471 (13)	0.64937 (14)	0.0543 (8)
C7	0.0403 (7)	0.48937 (15)	0.59035 (15)	0.0658 (9)
H7A	0.2281	0.476	0.5933	0.079*
H7B	0.0315	0.519	0.5602	0.079*
C8	−0.1418 (8)	0.44063 (16)	0.57049 (18)	0.0830 (12)
H8A	−0.0827	0.4265	0.5327	0.124*
H8B	−0.3277	0.4537	0.5665	0.124*
H8C	−0.1307	0.4106	0.5995	0.124*
O9	−0.2171 (5)	0.49645 (10)	0.68000 (10)	0.0699 (7)
C10	0.5820 (6)	0.67000 (13)	0.62685 (13)	0.0532 (8)
C11	0.6938 (7)	0.65374 (13)	0.57238 (14)	0.0571 (8)
C12	0.8825 (7)	0.68729 (15)	0.54402 (15)	0.0654 (9)
H12	0.9499	0.6755	0.5076	0.079*
C13	0.9730 (7)	0.73805 (15)	0.56867 (17)	0.0640 (9)
C14	0.8683 (7)	0.75504 (14)	0.62281 (16)	0.0657 (10)
H14	0.9278	0.7889	0.6402	0.079*
C15	0.6766 (7)	0.72210 (14)	0.65103 (15)	0.0605 (9)
O16	0.6203 (5)	0.60455 (10)	0.54461 (10)	0.0770 (8)
H16	0.5078	0.5877	0.5646	0.115*
C17	1.1739 (8)	0.77503 (17)	0.53729 (18)	0.0844 (12)
H17A	1.2123	0.8083	0.5609	0.127*
H17B	1.0976	0.7863	0.4992	0.127*
H17C	1.3404	0.7542	0.5317	0.127*
O18	0.5648 (6)	0.73696 (10)	0.70381 (11)	0.0824 (8)
C19	0.6523 (9)	0.78764 (16)	0.73329 (19)	0.0842 (12)
H19A	0.6385	0.8197	0.7061	0.101*
H19B	0.842	0.7839	0.7467	0.101*
C20	0.4748 (8)	0.79714 (18)	0.78508 (18)	0.0758 (11)
C21	0.3242 (9)	0.8464 (2)	0.7888 (2)	0.0907 (13)
H21	0.3401	0.8733	0.7586	0.109*
C22	0.1532 (11)	0.8579 (3)	0.8341 (3)	0.1063 (15)
H22	0.0572	0.8921	0.8352	0.128*
C23	0.1262 (10)	0.8189 (3)	0.8770 (3)	0.1106 (17)
H23	0.0065	0.8262	0.9077	0.133*
C24	0.2689 (13)	0.7684 (3)	0.8775 (2)	0.1151 (17)
H24	0.2502	0.742	0.908	0.138*
C25	0.4458 (10)	0.7582 (2)	0.8295 (2)	0.0996 (14)
H25	0.5438	0.7242	0.8283	0.12*
C26	0.1172 (6)	0.56381 (12)	0.78105 (13)	0.0485 (8)
C27	0.0104 (7)	0.58758 (14)	0.83107 (14)	0.0611 (9)
H27	−0.1031	0.6192	0.827	0.073*
C28	0.0657 (8)	0.56612 (15)	0.88733 (15)	0.0690 (10)
C29	0.2329 (8)	0.51930 (16)	0.89386 (15)	0.0690 (10)
H29	0.2723	0.5044	0.9315	0.083*
C30	0.3422 (7)	0.49453 (13)	0.84349 (15)	0.0603 (9)
C31	0.2878 (6)	0.51677 (13)	0.78742 (14)	0.0546 (8)
H31	0.365	0.5003	0.7541	0.065*
C32	−0.0504 (12)	0.5936 (2)	0.94053 (18)	0.0946 (14)
C36	0.5136 (10)	0.44223 (17)	0.8505 (2)	0.0807 (12)
F37	0.3614 (6)	0.39586 (11)	0.85326 (17)	0.1375 (12)
F38	0.6768 (7)	0.43269 (13)	0.80719 (16)	0.1480 (14)
F39	0.6615 (8)	0.44101 (13)	0.89967 (16)	0.1546 (14)
F33	−0.1600 (12)	0.56096 (17)	0.97657 (17)	0.219 (3)
F34	0.1149 (8)	0.6254 (3)	0.9680 (2)	0.235 (3)
F35	−0.2551 (10)	0.6284 (2)	0.92844 (15)	0.190 (2)

	U11	U22	U33	U12	U13	U23
N1	0.0651 (17)	0.0526 (16)	0.0442 (15)	−0.0098 (13)	0.0082 (12)	0.0046 (12)
N2	0.0614 (16)	0.0565 (17)	0.0448 (15)	−0.0068 (13)	0.0004 (12)	0.0073 (12)
C3	0.0554 (18)	0.0452 (18)	0.0480 (18)	0.0006 (14)	−0.0038 (14)	0.0049 (14)
C4	0.071 (2)	0.0496 (18)	0.054 (2)	0.0050 (15)	0.0087 (16)	0.0039 (15)
C5	0.0540 (18)	0.0507 (18)	0.0499 (18)	0.0048 (14)	0.0050 (14)	0.0034 (14)
C6	0.0599 (19)	0.0476 (18)	0.055 (2)	−0.0019 (15)	0.0010 (16)	0.0059 (15)
C7	0.074 (2)	0.064 (2)	0.059 (2)	−0.0114 (17)	0.0156 (17)	−0.0002 (16)
C8	0.091 (3)	0.076 (3)	0.083 (3)	−0.017 (2)	0.015 (2)	−0.023 (2)
O9	0.0737 (15)	0.0703 (16)	0.0666 (16)	−0.0161 (12)	0.0206 (12)	0.0007 (12)
C10	0.0591 (19)	0.0504 (18)	0.0498 (19)	−0.0019 (15)	0.0004 (15)	0.0066 (14)
C11	0.067 (2)	0.0492 (18)	0.055 (2)	−0.0003 (16)	−0.0012 (16)	0.0047 (16)
C12	0.073 (2)	0.065 (2)	0.059 (2)	−0.0020 (18)	0.0139 (17)	0.0091 (17)
C13	0.062 (2)	0.059 (2)	0.071 (2)	−0.0037 (17)	0.0012 (17)	0.0181 (18)
C14	0.080 (2)	0.0501 (19)	0.067 (2)	−0.0122 (17)	0.0000 (19)	0.0046 (16)
C15	0.066 (2)	0.059 (2)	0.056 (2)	−0.0091 (16)	−0.0026 (16)	0.0033 (16)
O16	0.0990 (19)	0.0673 (16)	0.0659 (16)	−0.0194 (13)	0.0254 (13)	−0.0101 (12)
C17	0.084 (3)	0.077 (3)	0.093 (3)	−0.017 (2)	0.012 (2)	0.022 (2)
O18	0.108 (2)	0.0729 (17)	0.0669 (17)	−0.0386 (14)	0.0217 (14)	−0.0174 (13)
C19	0.094 (3)	0.067 (2)	0.092 (3)	−0.022 (2)	0.011 (2)	−0.020 (2)
C20	0.082 (3)	0.070 (3)	0.075 (3)	−0.015 (2)	−0.001 (2)	−0.019 (2)
C21	0.095 (3)	0.089 (3)	0.089 (3)	−0.005 (3)	0.003 (2)	−0.026 (2)
C22	0.112 (4)	0.104 (4)	0.103 (4)	−0.005 (3)	0.006 (3)	−0.019 (3)
C23	0.100 (4)	0.123 (5)	0.109 (4)	−0.007 (3)	0.007 (3)	−0.048 (4)
C24	0.147 (5)	0.117 (4)	0.081 (4)	−0.023 (4)	0.004 (3)	−0.006 (3)
C25	0.112 (4)	0.094 (3)	0.093 (4)	−0.004 (3)	0.000 (3)	−0.011 (3)
C26	0.0526 (18)	0.0464 (17)	0.0467 (18)	−0.0022 (13)	0.0056 (14)	0.0002 (13)
C27	0.072 (2)	0.0548 (19)	0.057 (2)	0.0073 (16)	0.0118 (17)	0.0005 (16)
C28	0.095 (3)	0.063 (2)	0.050 (2)	0.003 (2)	0.0152 (18)	−0.0002 (17)
C29	0.090 (3)	0.069 (2)	0.048 (2)	−0.011 (2)	0.0017 (18)	0.0079 (17)
C30	0.071 (2)	0.0503 (19)	0.060 (2)	−0.0009 (16)	0.0009 (17)	0.0112 (16)
C31	0.0609 (19)	0.0533 (19)	0.0497 (19)	0.0025 (15)	0.0049 (15)	0.0012 (15)
C32	0.141 (4)	0.098 (3)	0.046 (2)	0.014 (3)	0.010 (3)	−0.008 (2)
C36	0.099 (3)	0.065 (3)	0.078 (3)	0.011 (2)	−0.009 (3)	0.018 (2)
F37	0.136 (2)	0.0594 (16)	0.216 (3)	0.0071 (15)	−0.006 (2)	0.0306 (18)
F38	0.167 (3)	0.128 (2)	0.152 (3)	0.088 (2)	0.065 (2)	0.053 (2)
F39	0.187 (3)	0.125 (2)	0.148 (3)	0.057 (2)	−0.078 (2)	0.0105 (19)
F33	0.400 (7)	0.148 (3)	0.119 (3)	0.008 (4)	0.160 (4)	−0.001 (2)
F34	0.156 (3)	0.362 (7)	0.188 (4)	−0.068 (4)	0.061 (3)	−0.206 (5)
F35	0.242 (4)	0.229 (4)	0.102 (2)	0.119 (4)	0.033 (3)	−0.038 (2)

N1—C6	1.360 (4)	C17—H17C	0.96
N1—N2	1.392 (3)	O18—C19	1.421 (4)
N1—C5	1.464 (4)	C19—C20	1.484 (5)
N2—C3	1.295 (4)	C19—H19A	0.97
C3—C10	1.464 (4)	C19—H19B	0.97
C3—C4	1.495 (4)	C20—C25	1.362 (6)
C4—C5	1.541 (4)	C20—C21	1.374 (6)
C4—H4A	0.97	C21—C22	1.359 (6)
C4—H4B	0.97	C21—H21	0.93
C5—C26	1.517 (4)	C22—C23	1.338 (7)
C5—H5	0.98	C22—H22	0.93
C6—O9	1.214 (4)	C23—C24	1.376 (8)
C6—C7	1.506 (5)	C23—H23	0.93
C7—C8	1.509 (5)	C24—C25	1.418 (7)
C7—H7A	0.97	C24—H24	0.93
C7—H7B	0.97	C25—H25	0.93
C8—H8A	0.96	C26—C27	1.368 (4)
C8—H8B	0.96	C26—C31	1.388 (4)
C8—H8C	0.96	C27—C28	1.379 (5)
C10—C11	1.404 (4)	C27—H27	0.93
C10—C15	1.411 (4)	C28—C29	1.374 (5)
C11—O16	1.356 (4)	C28—C32	1.482 (5)
C11—C12	1.380 (5)	C29—C30	1.390 (5)
C12—C13	1.381 (5)	C29—H29	0.93
C12—H12	0.93	C30—C31	1.381 (4)
C13—C14	1.389 (5)	C30—C36	1.492 (5)
C13—C17	1.499 (5)	C31—H31	0.93
C14—C15	1.380 (5)	C32—F33	1.244 (6)
C14—H14	0.93	C32—F34	1.251 (6)
C15—O18	1.362 (4)	C32—F35	1.315 (6)
O16—H16	0.82	C36—F38	1.291 (5)
C17—H17A	0.96	C36—F39	1.303 (5)
C17—H17B	0.96	C36—F37	1.320 (5)
C6—N1—N2	122.0 (3)	H17A—C17—H17C	109.5
C6—N1—C5	123.7 (3)	H17B—C17—H17C	109.5
N2—N1—C5	112.0 (2)	C15—O18—C19	119.7 (3)
C3—N2—N1	109.7 (2)	O18—C19—C20	108.4 (3)
N2—C3—C10	119.6 (3)	O18—C19—H19A	110
N2—C3—C4	112.7 (3)	C20—C19—H19A	110
C10—C3—C4	127.7 (3)	O18—C19—H19B	110
C3—C4—C5	103.3 (2)	C20—C19—H19B	110
C3—C4—H4A	111.1	H19A—C19—H19B	108.4
C5—C4—H4A	111.1	C25—C20—C21	117.1 (4)
C3—C4—H4B	111.1	C25—C20—C19	123.0 (4)
C5—C4—H4B	111.1	C21—C20—C19	119.9 (4)
H4A—C4—H4B	109.1	C22—C21—C20	123.5 (5)
N1—C5—C26	114.8 (2)	C22—C21—H21	118.2
N1—C5—C4	102.3 (2)	C20—C21—H21	118.2
C26—C5—C4	111.5 (2)	C23—C22—C21	118.5 (5)
N1—C5—H5	109.3	C23—C22—H22	120.8
C26—C5—H5	109.3	C21—C22—H22	120.8
C4—C5—H5	109.3	C22—C23—C24	122.4 (5)
O9—C6—N1	119.9 (3)	C22—C23—H23	118.8
O9—C6—C7	123.9 (3)	C24—C23—H23	118.8
N1—C6—C7	116.2 (3)	C23—C24—C25	117.3 (5)
C6—C7—C8	113.8 (3)	C23—C24—H24	121.4
C6—C7—H7A	108.8	C25—C24—H24	121.4
C8—C7—H7A	108.8	C20—C25—C24	121.2 (5)
C6—C7—H7B	108.8	C20—C25—H25	119.4
C8—C7—H7B	108.8	C24—C25—H25	119.4
H7A—C7—H7B	107.7	C27—C26—C31	118.7 (3)
C7—C8—H8A	109.5	C27—C26—C5	117.8 (3)
C7—C8—H8B	109.5	C31—C26—C5	123.3 (3)
H8A—C8—H8B	109.5	C26—C27—C28	122.1 (3)
C7—C8—H8C	109.5	C26—C27—H27	118.9
H8A—C8—H8C	109.5	C28—C27—H27	118.9
H8B—C8—H8C	109.5	C29—C28—C27	119.4 (3)
C11—C10—C15	116.1 (3)	C29—C28—C32	120.0 (3)
C11—C10—C3	121.4 (3)	C27—C28—C32	120.6 (4)
C15—C10—C3	122.5 (3)	C28—C29—C30	119.2 (3)
O16—C11—C12	116.5 (3)	C28—C29—H29	120.4
O16—C11—C10	121.8 (3)	C30—C29—H29	120.4
C12—C11—C10	121.7 (3)	C31—C30—C29	120.9 (3)
C11—C12—C13	121.2 (3)	C31—C30—C36	120.1 (3)
C11—C12—H12	119.4	C29—C30—C36	119.0 (3)
C13—C12—H12	119.4	C30—C31—C26	119.7 (3)
C12—C13—C14	118.5 (3)	C30—C31—H31	120.2
C12—C13—C17	121.2 (4)	C26—C31—H31	120.2
C14—C13—C17	120.3 (3)	F33—C32—F34	109.3 (5)
C15—C14—C13	120.6 (3)	F33—C32—F35	100.3 (5)
C15—C14—H14	119.7	F34—C32—F35	101.9 (5)
C13—C14—H14	119.7	F33—C32—C28	115.8 (4)
O18—C15—C14	123.2 (3)	F34—C32—C28	113.7 (5)
O18—C15—C10	114.9 (3)	F35—C32—C28	114.2 (4)
C14—C15—C10	121.9 (3)	F38—C36—F39	107.1 (4)
C11—O16—H16	109.5	F38—C36—F37	104.6 (4)
C13—C17—H17A	109.5	F39—C36—F37	104.0 (3)
C13—C17—H17B	109.5	F38—C36—C30	114.8 (3)
H17A—C17—H17B	109.5	F39—C36—C30	113.8 (4)
C13—C17—H17C	109.5	F37—C36—C30	111.6 (4)
N1—C6—C7—C8	−179.7 (3)	C15—O18—C19—C20	173.2 (3)
C14—C15—O18—C19	−2.2 (5)	O18—C19—C20—C21	−120.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O16—H16···N2	0.82	1.84	2.568 (3)	147
C31—H31···O9i	0.93	2.67	3.490 (4)	148
C21—H21···F37ii	0.93	2.72	3.488 (6)	140
C29—H29···F33iii	0.93	2.64	3.490 (5)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O16—H16⋯N2	0.82	1.84	2.568 (3)	147
C31—H31⋯O9i	0.93	2.67	3.490 (4)	148
C21—H21⋯F37ii	0.93	2.72	3.488 (6)	140
C29—H29⋯F33iii	0.93	2.64	3.490 (5)	152

Symmetry codes: (i) ; (ii) ; (iii) .