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Acta Cryst. (2009). E65, o1525-o1526    [ doi:10.1107/S1600536809020595 ]

Tris(2-methoxyphenyl)phosphine

O. bin Shawkataly, M. A. A. Pankhi, I. A. Khan, C. S. Yeap and H.-K. Fun

Abstract top

In the title compound, C21H21O3P, the whole molecule is disordered over two sets of positions with refined occupancies of 0.503 (1) and 0.497 (1). The dihedral angles between the three benzene rings are 72.9 (2)°, 82.9 (3)° and 70.0 (2)° in the major disorder component and the corresponding angles in the minor disorder component are 85.0 (2)°, 79.2 (2)° and 72.3 (2)°. The crystal structure is stabilized by C-H...[pi] interactions.

Comment top

The structure determination of the title compound was undertaken as part of a project to study the stereochemistry of substituted triphenylphosphine ligands (Abbassioun et al., 1990; Shawkataly et al., 1996; Hirsivaara et al., 2000; Barnes et al., 2006; Bott et al., 2007). Some of these interesting complexes have been synthesized using this tripodal ligand. Specially, its complex with platinum exhibits fluxionality and has been shown to behave as molecular gears (Romeo et al., 2006). The X-ray crystal structure of its thio analogue namely, tris[2-(methylsulfanyl)phenyl]phosphine, shows two independent molecules (Uttecht et al., 2005).

The whole molecule of title compound is disordered over two positions (Fig. 1 and 2) with refined occupancies of 0.503 (1) and 0.497 (1). The P—C bond lengths and C—P—C angles are comparable to a related structure (Uttecht et al., 2005). Bond lengths (Allen et al., 1987) and angles are within normal ranges. The dihedral angles between the benzene rings C1-C6 (A), C7-C12 (B) and C13-C18 (C) are: A/B 72.9 (2)°, A/C 82.9 (3)° and B/C 70.0 (2)° for the major disorder component, and A/B 85.0 (2)°, A/C 79.2 (2)° and B/C 72.3 (2)° for the minor disorder component.

In the crystal structure, a C18B···C19B(x,1+y,z) contact [3.112 (6) Å], shorter than the sum of the van der Waals radii is observed. The crystal structure (Fig. 3) is stabilized by C—H···π interactions (Table 1).

Related literature top

For P–C bond lengths and C–P–C angles, see: Uttecht et al. (2005). For the stereochemistry of tris(2-methoxyphenyl) phosphine complexes and for P–C bond distances, see: Abbassioun et al. (1990); Shawkataly et al. (1996); Hirsivaara et al. (2000); Barnes et al. (2006); Bott et al. (2007); Romeo et al. (2006). For bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).Cg1 is the centroid of the C13A-C18A ring.

Experimental top

The title compound was supplied by Strem Chemicals. Single crystals of were obtained by slow evaporation of an ethanol solution.

Refinement top

The whole molecule is disordered over positions, with occupancies of 0.503 (1) and 0.497 (1). The same Uij parameters were used for atom pairs C17A/C17B, C5A/C19B, C2A/C20A and C21B/C21A, and all disordered atoms were subjected to a rigid bond restraint. All H atoms were positioned geometrically and refined using a riding model with C-H = 0.93–0.96 Å and Uiso(H) = 1.2 and 1.5 Ueq(C). A rotating-group model was applied for the methyl groups.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids for non-H atoms. Both disorder components are shown.
[Figure 2] Fig. 2. The major disorder component of the title compound with atom labels and 50% probability displacement ellipsoids for non-H atoms.
[Figure 3] Fig. 3. The crystal packing of the title compound, showing molecular stacking down the b axis. Only the major disorder component is shown.
Tris(2-methoxyphenyl)phosphine top
Crystal data top
C21H21O3PF(000) = 1488
Mr = 352.35Dx = 1.297 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9954 reflections
a = 29.5721 (4) Åθ = 1.4–30.1°
b = 8.2201 (1) ŵ = 0.17 mm−1
c = 14.9409 (2) ÅT = 120 K
β = 96.381 (1)°Block, colourless
V = 3609.42 (8) Å30.47 × 0.37 × 0.11 mm
Z = 8
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		5318 independent reflections
Radiation source: fine-focus sealed tube4128 reflections with I > 2σ(I)
graphiteRint = 0.032
φ and ω scansθmax = 30.1°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −41→41
Tmin = 0.862, Tmax = 0.983k = −11→11
40913 measured reflectionsl = −21→18
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0605P)2 + 3.6006P]
where P = (Fo2 + 2Fc2)/3
5318 reflections(Δ/σ)max = 0.001
413 parametersΔρmax = 0.44 e Å−3
189 restraintsΔρmin = −0.50 e Å−3
Crystal data top
C21H21O3PV = 3609.42 (8) Å3
Mr = 352.35Z = 8
Monoclinic, C2/cMo Kα radiation
a = 29.5721 (4) ŵ = 0.17 mm−1
b = 8.2201 (1) ÅT = 120 K
c = 14.9409 (2) Å0.47 × 0.37 × 0.11 mm
β = 96.381 (1)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer		5318 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		4128 reflections with I > 2σ(I)
Tmin = 0.862, Tmax = 0.983Rint = 0.032
40913 measured reflectionsθmax = 30.1°
Refinement top
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.163Δρmax = 0.44 e Å−3
S = 1.05Δρmin = −0.50 e Å−3
5318 reflectionsAbsolute structure: ?
413 parametersFlack parameter: ?
189 restraintsRogers parameter: ?
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1)K.

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 > 2sigma(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 (Å2) top
xyzUiso*/UeqOcc. (<1)
P1A0.11821 (2)0.85263 (9)0.07264 (5)0.0284 (2)0.5033 (10)
O1A0.0996 (2)0.6755 (7)−0.0927 (3)0.0445 (10)0.5033 (10)
O2A0.21408 (13)0.8979 (6)0.1073 (3)0.0635 (12)0.5033 (10)
O3A0.05865 (9)1.1130 (3)0.1131 (2)0.0508 (7)0.5033 (10)
C1A0.13426 (11)0.6409 (4)0.0532 (2)0.0284 (7)0.5033 (10)
C2A0.12437 (10)0.5761 (4)−0.0329 (2)0.0410 (6)0.5033 (10)
C3A0.13987 (15)0.4212 (7)−0.0534 (3)0.0396 (16)0.5033 (10)
H3A0.13400.3806−0.11170.048*0.5033 (10)
C4A0.16347 (14)0.3302 (5)0.0115 (3)0.0595 (11)0.5033 (10)
H4A0.17400.2278−0.00280.071*0.5033 (10)
C5A0.1721 (3)0.3871 (7)0.0983 (5)0.0896 (14)0.5033 (10)
H5A0.18690.32130.14300.108*0.5033 (10)
C6A0.15860 (11)0.5437 (4)0.1188 (2)0.0382 (7)0.5033 (10)
H6A0.16580.58430.17670.046*0.5033 (10)
C7A0.14947 (10)0.8925 (3)0.18335 (19)0.0328 (6)0.5033 (10)
C8A0.19597 (13)0.9198 (5)0.1871 (3)0.0487 (9)0.5033 (10)
C9A0.2214 (2)0.9672 (7)0.2657 (5)0.0696 (17)0.5033 (10)
H9A0.25250.98450.26660.083*0.5033 (10)
C10A0.2007 (2)0.9887 (5)0.3428 (4)0.0812 (17)0.5033 (10)
H10A0.21791.02080.39580.097*0.5033 (10)
C11A0.1542 (2)0.9627 (5)0.3423 (3)0.0670 (14)0.5033 (10)
H11A0.14010.97740.39440.080*0.5033 (10)
C12A0.12902 (13)0.9143 (4)0.2622 (2)0.0424 (7)0.5033 (10)
H12A0.09790.89620.26130.051*0.5033 (10)
C13A0.05989 (10)0.8286 (4)0.1004 (2)0.0368 (7)0.5033 (10)
C14A0.03431 (14)0.9685 (5)0.1150 (3)0.0478 (10)0.5033 (10)
C15A−0.01091 (16)0.9581 (8)0.1305 (5)0.0642 (16)0.5033 (10)
H15A−0.02701.05150.14210.077*0.5033 (10)
C16A−0.03183 (13)0.8085 (6)0.1288 (4)0.0763 (15)0.5033 (10)
H16A−0.06270.80520.13590.092*0.5033 (10)
C17A−0.00931 (19)0.6586 (7)0.1167 (6)0.0678 (11)0.5033 (10)
H17A−0.02310.55740.11980.081*0.5033 (10)
C18A0.03710 (13)0.6805 (5)0.0990 (3)0.0491 (10)0.5033 (10)
H18A0.05320.58810.08550.059*0.5033 (10)
C19A0.09955 (16)0.6406 (6)−0.1872 (3)0.0579 (10)0.5033 (10)
H19A0.08640.7305−0.22200.087*0.5033 (10)
H19B0.08200.5442−0.20210.087*0.5033 (10)
H19C0.13020.6239−0.20060.087*0.5033 (10)
C20A0.25882 (15)0.9331 (7)0.1125 (3)0.0410 (6)0.5033 (10)
H20A0.27020.90510.05670.061*0.5033 (10)
H20B0.27490.87190.16070.061*0.5033 (10)
H20C0.26321.04730.12380.061*0.5033 (10)
C21A0.03439 (3)1.25999 (10)0.11792 (5)0.0859 (15)0.5033 (10)
H21A0.05491.35020.11610.129*0.5033 (10)
H21B0.02061.26310.17310.129*0.5033 (10)
H21C0.01111.26670.06780.129*0.5033 (10)
P1B0.12322 (2)0.74119 (9)0.15377 (5)0.0330 (2)0.4967 (10)
O1B0.16399 (2)0.44061 (9)0.10141 (7)0.0576 (9)0.4967 (10)
O2B0.16390 (2)0.92945 (9)0.30307 (6)0.0431 (6)0.4967 (10)
O3B0.02690 (3)0.71548 (10)0.13196 (9)0.0623 (10)0.4967 (10)
C1B0.11971 (6)0.65852 (15)0.03978 (5)0.0317 (9)0.4967 (10)
C2B0.14037 (6)0.50871 (15)0.02601 (5)0.0404 (7)0.4967 (10)
C3B0.13712 (6)0.43983 (16)−0.05953 (5)0.049 (2)0.4967 (10)
H3B0.14950.3373−0.06690.059*0.4967 (10)
C4B0.11634 (11)0.5190 (5)−0.1325 (3)0.0502 (9)0.4967 (10)
H4B0.11600.4736−0.18960.060*0.4967 (10)
C5B0.0956 (3)0.6672 (12)−0.1218 (4)0.0458 (14)0.4967 (10)
H5B0.08060.7207−0.17120.055*0.4967 (10)
C6B0.09754 (11)0.7356 (5)−0.0366 (2)0.0398 (7)0.4967 (10)
H6B0.08370.8357−0.03000.048*0.4967 (10)
C7B0.17805 (10)0.8463 (4)0.15924 (19)0.0283 (5)0.4967 (10)
C8B0.19367 (11)0.9314 (4)0.2379 (2)0.0318 (6)0.4967 (10)
C9B0.23494 (15)1.0121 (6)0.2487 (3)0.0418 (10)0.4967 (10)
H9B0.24421.06930.30120.050*0.4967 (10)
C10B0.26237 (11)1.0052 (5)0.1782 (3)0.0456 (8)0.4967 (10)
H10B0.29071.05590.18540.055*0.4967 (10)
C11B0.2480 (2)0.9209 (8)0.0934 (3)0.0656 (17)0.4967 (10)
H11B0.26520.92080.04500.079*0.4967 (10)
C12B0.20682 (16)0.8418 (5)0.0913 (3)0.0316 (8)0.4967 (10)
H12B0.19740.78040.04040.038*0.4967 (10)
C13B0.08356 (10)0.9123 (4)0.1363 (2)0.0348 (6)0.4967 (10)
C14B0.03738 (12)0.8789 (6)0.1299 (3)0.0453 (9)0.4967 (10)
C15B0.00492 (17)1.0010 (8)0.1214 (5)0.0577 (13)0.4967 (10)
H15B−0.02580.97510.11880.069*0.4967 (10)
C16B0.01844 (14)1.1617 (6)0.1170 (3)0.0656 (12)0.4967 (10)
H16B−0.00321.24410.10980.079*0.4967 (10)
C17B0.06457 (16)1.1998 (7)0.1235 (4)0.0678 (11)0.4967 (10)
H17B0.07411.30750.12190.081*0.4967 (10)
C18B0.09617 (11)1.0742 (4)0.1323 (3)0.0440 (8)0.4967 (10)
H18B0.12691.09980.13560.053*0.4967 (10)
C19B0.1803 (2)0.2818 (5)0.0964 (4)0.0896 (14)0.4967 (10)
H19D0.19030.24300.15600.134*0.4967 (10)
H19E0.20550.28060.06090.134*0.4967 (10)
H19F0.15650.21280.06900.134*0.4967 (10)
C20B0.17636 (17)1.0245 (6)0.3812 (3)0.0588 (11)0.4967 (10)
H20D0.15241.02120.41950.088*0.4967 (10)
H20E0.18141.13500.36390.088*0.4967 (10)
H20F0.20380.98170.41300.088*0.4967 (10)
C21B−0.0196 (2)0.6854 (9)0.1278 (7)0.0859 (15)0.4967 (10)
H21D−0.02450.57210.13890.129*0.4967 (10)
H21E−0.03400.71390.06920.129*0.4967 (10)
H21F−0.03230.74940.17260.129*0.4967 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P1A0.0297 (4)0.0262 (3)0.0281 (4)−0.0024 (3)−0.0023 (3)0.0026 (3)
O1A0.0543 (19)0.0487 (17)0.027 (2)0.0000 (13)−0.0113 (18)−0.0048 (19)
O2A0.0242 (14)0.087 (3)0.078 (3)−0.0219 (18)0.0018 (14)−0.006 (2)
O3A0.0461 (14)0.0345 (13)0.0688 (18)0.0072 (11)−0.0076 (12)−0.0080 (13)
C1A0.0191 (17)0.0299 (15)0.0361 (15)−0.0035 (12)0.0023 (12)−0.0003 (12)
C2A0.0290 (11)0.0477 (14)0.0449 (15)−0.0056 (10)−0.0015 (10)−0.0047 (12)
C3A0.027 (3)0.036 (2)0.056 (3)−0.003 (2)0.005 (3)−0.017 (2)
C4A0.056 (2)0.0375 (19)0.082 (3)0.0108 (16)−0.007 (2)−0.0184 (18)
C5A0.116 (3)0.0338 (17)0.107 (3)0.0211 (19)−0.043 (2)−0.0097 (19)
C6A0.0366 (15)0.0336 (16)0.0415 (17)−0.0010 (13)−0.0092 (12)−0.0011 (13)
C7A0.0393 (15)0.0248 (13)0.0319 (14)−0.0029 (11)−0.0060 (11)0.0028 (11)
C8A0.046 (2)0.042 (2)0.053 (2)−0.0104 (16)−0.0172 (18)−0.002 (2)
C9A0.067 (4)0.049 (3)0.082 (4)−0.015 (2)−0.041 (3)−0.004 (3)
C10A0.130 (4)0.042 (2)0.058 (3)−0.005 (3)−0.053 (3)−0.008 (2)
C11A0.132 (4)0.0335 (19)0.031 (2)0.011 (2)−0.012 (2)−0.0032 (16)
C12A0.066 (2)0.0300 (15)0.0304 (15)0.0059 (15)0.0016 (14)0.0025 (12)
C13A0.0255 (13)0.0363 (16)0.0472 (17)0.0038 (12)−0.0016 (13)−0.0010 (13)
C14A0.036 (2)0.041 (2)0.063 (2)0.0114 (17)−0.0115 (16)−0.0106 (19)
C15A0.033 (3)0.065 (3)0.093 (4)0.014 (2)−0.001 (3)−0.029 (3)
C16A0.0260 (16)0.079 (3)0.125 (4)0.0004 (18)0.012 (2)−0.023 (3)
C17A0.0469 (18)0.0447 (19)0.112 (3)0.0060 (14)0.0080 (18)−0.012 (2)
C18A0.0349 (18)0.042 (2)0.072 (3)−0.0057 (15)0.0116 (17)−0.0071 (19)
C19A0.075 (3)0.066 (3)0.0310 (18)−0.014 (2)−0.0030 (17)−0.0049 (17)
C20A0.0290 (11)0.0477 (14)0.0449 (15)−0.0056 (10)−0.0015 (10)−0.0047 (12)
C21A0.054 (2)0.050 (2)0.152 (4)0.0102 (16)0.004 (2)−0.025 (2)
P1B0.0320 (4)0.0339 (4)0.0334 (4)−0.0019 (3)0.0054 (3)0.0063 (3)
O1B0.072 (2)0.0230 (16)0.0701 (19)−0.0038 (14)−0.0264 (16)0.0008 (15)
O2B0.0494 (14)0.0543 (16)0.0261 (12)0.0026 (12)0.0058 (11)−0.0029 (11)
O3B0.0374 (15)0.0579 (19)0.097 (3)−0.0119 (13)0.0295 (15)−0.0223 (18)
C1B0.0204 (19)0.0321 (17)0.0430 (19)−0.0036 (13)0.0049 (14)−0.0003 (14)
C2B0.0299 (14)0.0284 (15)0.061 (2)−0.0059 (12)−0.0030 (14)−0.0048 (14)
C3B0.031 (4)0.044 (4)0.070 (4)−0.005 (3)0.000 (3)−0.019 (3)
C4B0.0298 (15)0.069 (2)0.054 (2)−0.0125 (15)0.0124 (14)−0.0253 (19)
C5B0.037 (2)0.065 (3)0.033 (3)0.003 (2)−0.004 (2)−0.008 (3)
C6B0.0355 (15)0.0464 (19)0.0373 (17)0.0073 (14)0.0034 (13)−0.0022 (15)
C7B0.0272 (13)0.0298 (14)0.0267 (13)0.0029 (12)−0.0021 (11)0.0033 (11)
C8B0.0336 (16)0.0348 (16)0.0257 (14)0.0069 (13)−0.0026 (13)0.0011 (13)
C9B0.038 (2)0.046 (3)0.039 (2)0.0000 (17)−0.0068 (15)−0.0147 (19)
C10B0.0288 (14)0.052 (2)0.055 (2)−0.0071 (14)−0.0022 (13)−0.0116 (17)
C11B0.065 (3)0.080 (3)0.042 (2)−0.003 (3)−0.036 (2)−0.022 (2)
C12B0.032 (2)0.0327 (19)0.0288 (16)0.0021 (15)−0.0001 (13)−0.0029 (13)
C13B0.0293 (13)0.0415 (16)0.0347 (15)0.0021 (12)0.0076 (11)0.0003 (13)
C14B0.0299 (17)0.053 (2)0.055 (2)0.0015 (17)0.0109 (15)−0.015 (2)
C15B0.027 (2)0.075 (3)0.074 (3)0.008 (2)0.014 (2)−0.014 (3)
C16B0.045 (2)0.075 (3)0.076 (3)0.025 (2)0.006 (2)−0.003 (2)
C17B0.0469 (18)0.0447 (19)0.112 (3)0.0060 (14)0.0080 (18)−0.012 (2)
C18B0.0347 (15)0.0408 (17)0.056 (2)0.0024 (13)0.0034 (14)0.0090 (15)
C19B0.116 (3)0.0338 (17)0.107 (3)0.0211 (19)−0.043 (2)−0.0097 (19)
C20B0.073 (3)0.067 (3)0.038 (2)0.004 (2)0.0107 (19)−0.013 (2)
C21B0.054 (2)0.050 (2)0.152 (4)0.0102 (16)0.004 (2)−0.025 (2)
Geometric parameters (Å, °) top
P1A—C1A1.836 (4)P1B—C1B1.8258
P1A—C7A1.833 (3)P1B—C7B1.831 (3)
P1A—C13A1.829 (3)P1B—C13B1.831 (3)
O1A—C2A1.362 (6)O1B—C2B1.3767
O1A—C19A1.440 (4)O1B—C19B1.397 (4)
O2A—C20A1.348 (5)O2B—C8B1.383 (3)
O2A—C8A1.373 (6)O2B—C20B1.419 (4)
O3A—C14A1.392 (5)O3B—C14B1.379 (5)
O3A—C21A1.411 (3)O3B—C21B1.390 (6)
C1A—C2A1.393 (5)C1B—C2B1.400
C1A—C6A1.400 (5)C1B—C6B1.403 (3)
C2A—C3A1.399 (6)C2B—C3B1.3914
C3A—C4A1.356 (7)C3B—C4B1.357 (5)
C3A—H3A0.93C3B—H3B0.93
C4A—C5A1.375 (8)C4B—C5B1.381 (9)
C4A—H4A0.93C4B—H4B0.93
C5A—C6A1.392 (6)C5B—C6B1.386 (6)
C5A—H5A0.93C5B—H5B0.93
C6A—H6A0.93C6B—H6B0.93
C7A—C8A1.388 (5)C7B—C12B1.395 (5)
C7A—C12A1.394 (4)C7B—C8B1.402 (4)
C8A—C9A1.379 (7)C8B—C9B1.383 (5)
C9A—C10A1.375 (9)C9B—C10B1.400 (6)
C9A—H9A0.93C9B—H9B0.93
C10A—C11A1.390 (8)C10B—C11B1.465 (5)
C10A—H10A0.93C10B—H10B0.93
C11A—C12A1.396 (5)C11B—C12B1.377 (7)
C11A—H11A0.93C11B—H11B0.93
C12A—H12A0.93C12B—H12B0.93
C13A—C18A1.391 (5)C13B—C18B1.386 (5)
C13A—C14A1.406 (5)C13B—C14B1.386 (4)
C14A—C15A1.385 (6)C14B—C15B1.385 (7)
C15A—C16A1.375 (7)C15B—C16B1.385 (8)
C15A—H15A0.93C15B—H15B0.93
C16A—C17A1.421 (6)C16B—C17B1.392 (6)
C16A—H16A0.93C16B—H16B0.93
C17A—C18A1.437 (6)C17B—C18B1.389 (6)
C17A—H17A0.93C17B—H17B0.93
C18A—H18A0.93C18B—H18B0.93
C19A—H19A0.96C19B—H19D0.96
C19A—H19B0.96C19B—H19E0.96
C19A—H19C0.96C19B—H19F0.96
C20A—H20A0.96C20B—H20D0.96
C20A—H20B0.96C20B—H20E0.96
C20A—H20C0.96C20B—H20F0.96
C21A—H21A0.96C21B—H21D0.96
C21A—H21B0.96C21B—H21E0.96
C21A—H21C0.96C21B—H21F0.96
C7A—P1A—C1A101.47 (14)O1B—C2B—C3B124.3
C13A—P1A—C1A101.57 (15)O1B—C2B—C1B115.3
C13A—P1A—C7A102.02 (15)C3B—C2B—C1B120.4
C2A—O1A—C19A117.8 (5)C4B—C3B—C2B121.44 (16)
C20A—O2A—C8A113.4 (4)C4B—C3B—H3B119.3
C14A—O3A—C21A117.6 (3)C2B—C3B—H3B119.3
C2A—C1A—C6A117.8 (3)C3B—C4B—C5B119.8 (3)
C2A—C1A—P1A118.5 (3)C3B—C4B—H4B120.1
C6A—C1A—P1A123.5 (3)C5B—C4B—H4B120.1
O1A—C2A—C1A114.8 (3)C4B—C5B—C6B119.4 (5)
O1A—C2A—C3A124.5 (4)C4B—C5B—H5B120.3
C1A—C2A—C3A120.7 (4)C6B—C5B—H5B120.3
C4A—C3A—C2A120.0 (4)C5B—C6B—C1B122.1 (4)
C4A—C3A—H3A120.0C5B—C6B—H6B118.9
C2A—C3A—H3A120.0C1B—C6B—H6B118.9
C3A—C4A—C5A120.9 (4)C12B—C7B—C8B116.9 (3)
C3A—C4A—H4A119.5C12B—C7B—P1B124.3 (3)
C5A—C4A—H4A119.5C8B—C7B—P1B118.7 (2)
C4A—C5A—C6A119.6 (5)C9B—C8B—O2B123.1 (3)
C4A—C5A—H5A120.2C9B—C8B—C7B122.8 (3)
C6A—C5A—H5A120.2O2B—C8B—C7B114.1 (3)
C5A—C6A—C1A120.8 (4)C8B—C9B—C10B118.1 (4)
C5A—C6A—H6A119.6C8B—C9B—H9B121.0
C1A—C6A—H6A119.6C10B—C9B—H9B121.0
C8A—C7A—C12A117.8 (3)C9B—C10B—C11B122.2 (4)
C8A—C7A—P1A117.6 (3)C9B—C10B—H10B118.9
C12A—C7A—P1A124.2 (3)C11B—C10B—H10B118.9
O2A—C8A—C9A123.3 (5)C12B—C11B—C10B114.4 (5)
O2A—C8A—C7A115.1 (4)C12B—C11B—H11B122.8
C9A—C8A—C7A121.6 (5)C10B—C11B—H11B122.8
C10A—C9A—C8A119.9 (6)C11B—C12B—C7B125.5 (4)
C10A—C9A—H9A120.1C11B—C12B—H12B117.3
C8A—C9A—H9A120.1C7B—C12B—H12B117.3
C9A—C10A—C11A120.5 (4)C18B—C13B—C14B117.1 (3)
C9A—C10A—H10A119.7C18B—C13B—P1B124.9 (2)
C11A—C10A—H10A119.7C14B—C13B—P1B117.9 (3)
C10A—C11A—C12A118.8 (5)O3B—C14B—C15B123.5 (3)
C10A—C11A—H11A120.6O3B—C14B—C13B114.4 (3)
C12A—C11A—H11A120.6C15B—C14B—C13B122.0 (4)
C7A—C12A—C11A121.4 (4)C16B—C15B—C14B119.7 (4)
C7A—C12A—H12A119.3C16B—C15B—H15B120.2
C11A—C12A—H12A119.3C14B—C15B—H15B120.2
C18A—C13A—C14A116.7 (3)C15B—C16B—C17B119.8 (4)
C18A—C13A—P1A124.0 (3)C15B—C16B—H16B120.1
C14A—C13A—P1A119.0 (3)C17B—C16B—H16B120.1
C15A—C14A—O3A124.6 (4)C18B—C17B—C16B118.9 (5)
C15A—C14A—C13A121.4 (4)C18B—C17B—H17B120.5
O3A—C14A—C13A114.0 (3)C16B—C17B—H17B120.5
C16A—C15A—C14A119.5 (5)C13B—C18B—C17B122.5 (4)
C16A—C15A—H15A120.3C13B—C18B—H18B118.8
C14A—C15A—H15A120.3C17B—C18B—H18B118.8
C15A—C16A—C17A124.1 (4)O1B—C19B—H19D109.5
C15A—C16A—H16A117.9O1B—C19B—H19E109.5
C17A—C16A—H16A117.9H19D—C19B—H19E109.5
C16A—C17A—C18A112.7 (5)O1B—C19B—H19F109.5
C16A—C17A—H17A123.7H19D—C19B—H19F109.5
C18A—C17A—H17A123.7H19E—C19B—H19F109.5
C13A—C18A—C17A125.3 (4)O2B—C20B—H20D109.5
C13A—C18A—H18A117.4O2B—C20B—H20E109.5
C17A—C18A—H18A117.4H20D—C20B—H20E109.5
C1B—P1B—C7B100.11 (12)O2B—C20B—H20F109.5
C1B—P1B—C13B100.60 (10)H20D—C20B—H20F109.5
C7B—P1B—C13B101.19 (14)H20E—C20B—H20F109.5
C2B—O1B—C19B118.9 (2)O3B—C21B—H21D109.5
C8B—O2B—C20B116.4 (3)O3B—C21B—H21E109.5
C14B—O3B—C21B113.3 (3)H21D—C21B—H21E109.5
C2B—C1B—C6B116.71 (16)O3B—C21B—H21F109.5
C2B—C1B—P1B118.9H21D—C21B—H21F109.5
C6B—C1B—P1B124.34 (16)H21E—C21B—H21F109.5
C13A—P1A—C1A—C2A87.8 (3)C7B—P1B—C1B—C2B85.86 (10)
C7A—P1A—C1A—C2A−167.3 (3)C13B—P1B—C1B—C2B−170.61 (10)
C13A—P1A—C1A—C6A−96.6 (3)C7B—P1B—C1B—C6B−93.9 (2)
C7A—P1A—C1A—C6A8.4 (3)C13B—P1B—C1B—C6B9.6 (3)
C19A—O1A—C2A—C1A161.8 (4)C19B—O1B—C2B—C3B−9.9 (3)
C19A—O1A—C2A—C3A−17.4 (7)C19B—O1B—C2B—C1B171.4 (3)
C6A—C1A—C2A—O1A178.4 (4)C6B—C1B—C2B—O1B176.5 (2)
P1A—C1A—C2A—O1A−5.7 (5)P1B—C1B—C2B—O1B−3.3
C6A—C1A—C2A—C3A−2.3 (5)C6B—C1B—C2B—C3B−2.20 (18)
P1A—C1A—C2A—C3A173.6 (3)P1B—C1B—C2B—C3B177.99 (8)
O1A—C2A—C3A—C4A−178.6 (5)O1B—C2B—C3B—C4B−174.7 (2)
C1A—C2A—C3A—C4A2.2 (6)C1B—C2B—C3B—C4B3.85 (19)
C2A—C3A—C4A—C5A0.7 (8)C2B—C3B—C4B—C5B−3.6 (6)
C3A—C4A—C5A—C6A−3.5 (10)C3B—C4B—C5B—C6B1.9 (10)
C4A—C5A—C6A—C1A3.3 (9)C4B—C5B—C6B—C1B−0.3 (10)
C2A—C1A—C6A—C5A−0.4 (6)C2B—C1B—C6B—C5B0.5 (6)
P1A—C1A—C6A—C5A−176.1 (5)P1B—C1B—C6B—C5B−179.7 (5)
C13A—P1A—C7A—C8A−179.0 (3)C1B—P1B—C7B—C12B−4.2 (3)
C1A—P1A—C7A—C8A76.4 (3)C13B—P1B—C7B—C12B−107.2 (3)
C13A—P1A—C7A—C12A−6.2 (3)C1B—P1B—C7B—C8B178.8 (2)
C1A—P1A—C7A—C12A−110.8 (3)C13B—P1B—C7B—C8B75.8 (3)
C20A—O2A—C8A—C9A−2.4 (7)C20B—O2B—C8B—C9B4.0 (5)
C20A—O2A—C8A—C7A177.0 (4)C20B—O2B—C8B—C7B−175.1 (3)
C12A—C7A—C8A—O2A−179.4 (3)C12B—C7B—C8B—C9B1.7 (5)
P1A—C7A—C8A—O2A−6.1 (5)P1B—C7B—C8B—C9B178.9 (3)
C12A—C7A—C8A—C9A−0.1 (6)C12B—C7B—C8B—O2B−179.2 (3)
P1A—C7A—C8A—C9A173.3 (4)P1B—C7B—C8B—O2B−2.0 (3)
O2A—C8A—C9A—C10A179.2 (5)O2B—C8B—C9B—C10B179.8 (3)
C7A—C8A—C9A—C10A−0.1 (8)C7B—C8B—C9B—C10B−1.2 (6)
C8A—C9A—C10A—C11A0.1 (8)C8B—C9B—C10B—C11B2.2 (7)
C9A—C10A—C11A—C12A0.1 (7)C9B—C10B—C11B—C12B−3.7 (8)
C8A—C7A—C12A—C11A0.3 (5)C10B—C11B—C12B—C7B4.4 (8)
P1A—C7A—C12A—C11A−172.5 (3)C8B—C7B—C12B—C11B−3.6 (6)
C10A—C11A—C12A—C7A−0.3 (6)P1B—C7B—C12B—C11B179.4 (4)
C7A—P1A—C13A—C18A−107.9 (3)C1B—P1B—C13B—C18B−104.3 (3)
C1A—P1A—C13A—C18A−3.4 (4)C7B—P1B—C13B—C18B−1.7 (3)
C7A—P1A—C13A—C14A79.2 (3)C1B—P1B—C13B—C14B78.1 (3)
C1A—P1A—C13A—C14A−176.3 (3)C7B—P1B—C13B—C14B−179.2 (3)
C21A—O3A—C14A—C15A−6.9 (7)C21B—O3B—C14B—C15B−2.0 (7)
C21A—O3A—C14A—C13A173.7 (3)C21B—O3B—C14B—C13B178.4 (5)
C18A—C13A—C14A—C15A2.3 (7)C18B—C13B—C14B—O3B178.4 (3)
P1A—C13A—C14A—C15A175.8 (5)P1B—C13B—C14B—O3B−3.9 (4)
C18A—C13A—C14A—O3A−178.2 (4)C18B—C13B—C14B—C15B−1.2 (6)
P1A—C13A—C14A—O3A−4.8 (5)P1B—C13B—C14B—C15B176.5 (4)
O3A—C14A—C15A—C16A178.4 (5)O3B—C14B—C15B—C16B−177.9 (5)
C13A—C14A—C15A—C16A−2.2 (9)C13B—C14B—C15B—C16B1.6 (8)
C14A—C15A—C16A—C17A3.6 (11)C14B—C15B—C16B—C17B−1.7 (9)
C15A—C16A—C17A—C18A−4.8 (10)C15B—C16B—C17B—C18B1.4 (8)
C14A—C13A—C18A—C17A−4.1 (7)C14B—C13B—C18B—C17B0.9 (6)
P1A—C13A—C18A—C17A−177.1 (5)P1B—C13B—C18B—C17B−176.7 (4)
C16A—C17A—C18A—C13A5.1 (9)C16B—C17B—C18B—C13B−1.0 (7)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C21A—H21C···Cg1i0.962.833.662 (3)145
Symmetry codes: (i) x+1/2, y+5/2, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C21A—H21C···Cg1i0.962.833.662 (3)145
Symmetry codes: (i) x+1/2, y+5/2, z.
Acknowledgements top

The authors thank the Malaysian Government and Universiti Sains Malaysia for the Research grant No. 1001/PJJAUH/811115. HKF thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. CSY thanks the Malaysian Government and Universiti Sains Malaysia for the award of the post of Research Officer under the Science Fund grant No. 305/PFIZIK/613312.

references
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