A redetermination of (2-methoxy­phen­yl)diphenyl­phosphine

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

doi:10.1107/S1600536809038835

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages o2660-o2661

https://doi.org/10.1107/S1600536809038835

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A redetermination of (2-methoxyphenyl)diphenylphosphine

Omar bin Shawkataly,^a ^*‡ Mohd. Aslam A. Pankhi,^a Imthyaz Ahmed Khan,^a Chin Sing Yeap ^b § and Hoong-Kun Fun ^b ¶

^aChemical Sciences Programme, Centre for Distance Education, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: omarsa@usm.my

(Received 8 September 2009; accepted 25 September 2009; online 7 October 2009)

The asymmetric unit of the title triphenylphosphine compound, C₁₉H₁₇OP, consists of two crystallographically independent molecules with similar conformations. One of these two molecules has a whole-molecule disorder over two positions with refined occupancies of 0.753 (3) and 0.247 (3). The dihedral angles between the three benzene rings are 89.69 (7), 76.54 (7) and 86.02 (7)° in the non-disordered molecule and the corresponding angles are 88.3 (4), 83.2 (4) and 84.2 (3)° for the major component and 80.2 (11), 89.5 (11) and 74.4 (9)° for the minor component of the disordered molecule. This structure has been reported previously [Suomalainen et al. (2000 ). Eur. J. Inorg. Chem. pp. 2607–2613]; however, the disorder detailed here was not mentioned in that determination. In the crystal structure, the molecules are stacked down the b axis and stabilized by C—H⋯π interactions.

Related literature

For a previous report of this molecule, see: Suomalainen et al. (2000). For P–C bond lengths and C–P–C angles in related structures, see: Dunne & Orpen (1991 ); Shawkataly et al. (2009 ). For the stereochemistry of 2-methoxyphenyl diphenylphosphine complexes, see: Dahlenburg et al. (1997 ); Moreno et al. (2005 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₉H₁₇OP
M_r = 292.30
Monoclinic, C 2/c
a = 31.1813 (8) Å
b = 7.1474 (2) Å
c = 28.3025 (8) Å
β = 90.3795 (12)°
V = 6307.5 (3) Å³
Z = 16
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 100 K
0.78 × 0.24 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.879, T_max = 0.978
49460 measured reflections
11740 independent reflections
8873 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.123
S = 1.10
11740 reflections
566 parameters
157 restraints
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4A—H4AA⋯Cg1ⁱ	0.93	2.65	3.520 (9)	156
C4A—H4AA⋯Cg2ⁱ	0.93	2.58	3.471 (3)	159
C17A—H17A⋯Cg3ⁱⁱ	0.93	2.91	3.645 (8)	137
C10C—H10C⋯Cg4ⁱⁱ	0.93	2.78	3.561 (15)	142
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) -x-1, -y-1, -z. Cg1, Cg2 Cg3 and Cg4 are the centroids of the C13C–C18C, C7B–C12B, C7C–C12C and C13A–C18A benzene rings, respectively.

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; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809038835/sj2649sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809038835/sj2649Isup2.hkl

checkCIF report

Comment top

Substituted triphenylphosphines as well as the parent compound have found widespread use as ligands in transition-metal chemistry, notably in homogeneous catalysis. The structure of the title compound was reported by Suomalainen et al., (2000) for the first time. However, the whole-molecule disorder in one of the the two molecules in the asymmetric unit present in 2-methoxyphenyl diphenylphosphine (I) has not been reported. This resulted in large residual peaks in the difference map in his solution. This prompts us to redetermine the structure. Our redetermination has taken care of these large residual peaks which are the consequence of the whole-molecule disorder as shown in molecules B and C (Fig. 1, 2 & 3).

Interestingly, the evidence of the disorder in this ligand has however been reported by Moreno et al., (2005) in a ruthenium complex.

This study was taken up as part of a project to study the stereochemistry of substituted triphenylphosphine ligands.

The asymmetric unit of (I), consists of two crystallographically independent molecules, A and B/C, with similar conformation (Fig. 1, 2 & 3). Molecule B/C are the major/minor components of the whole-molecule disorder over two positions with refined occupancies of 0.753 (3) and 0.247 (3) respectively. The P–C bond lengths and C–P–C angles for the asymmetric unit are comparable to the related structures (Dunne & Orpen, 1991; Suomalainen et al., 2000; Shawkataly et al., 2009). The dihedral angles between the three benzene rings [C1A–C6A/C7A–C12A, C1A–C6A/C13A–C18A and C7A–C13A/C13A–C18A] are 89.69 (7), 76.54 (7) and 86.02 (7)° in molecule A and the corresponding angles for major B and minor C components of the whole-molecule are 88.3 (4), 83.2 (4), 84.2 (3)° and 80.2 (11), 89.5 (11), 74.4 (9)°, respectively.

In the crystal structure, the molecules are stacked down the b axis (Fig. 4) and stabilized by the C—H···π interactions (Table 1).

Related literature top

For a previous report of this molecule, see: Suomalainen et al. (2000). For P–C bond lengths and C–P–C angles in related structures, see: Dunne & Orpen (1991); Shawkataly et al. (2009). For the stereochemistry of 2-methoxyphenyl diphenylphosphine complexes, see: Dahlenburg et al. (1997); Moreno et al. (2005). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). Cg1, Cg2 Cg3 and Cg4 are the centroids of the C13C–C18C, C7B–C12B, C7C–C12C and C13A–C18A benzene rings, respectively.

Experimental top

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

Structure description top

Interestingly, the evidence of the disorder in this ligand has however been reported by Moreno et al., (2005) in a ruthenium complex.

This study was taken up as part of a project to study the stereochemistry of substituted triphenylphosphine ligands.

In the crystal structure, the molecules are stacked down the b axis (Fig. 4) and stabilized by the C—H···π interactions (Table 1).

For a previous report of this molecule, see: Suomalainen et al. (2000). For P–C bond lengths and C–P–C angles in related structures, see: Dunne & Orpen (1991); Shawkataly et al. (2009). For the stereochemistry of 2-methoxyphenyl diphenylphosphine complexes, see: Dahlenburg et al. (1997); Moreno et al. (2005). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). Cg1, Cg2 Cg3 and Cg4 are the centroids of the C13C–C18C, C7B–C12B, C7C–C12C and C13A–C18A benzene rings, respectively.

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

	Fig. 1. The molecular structure of the title compound with 30% probability ellipsoids for non-H atoms. Both disorder components are shown, with open bonds for the minor disorder component.
	Fig. 2. The molecular structure of the title compound with atoms label and 50% probability ellipsoids for non-H atoms. Only major disorder component is shown.
	Fig. 3. The molecular structure of the title compound with atoms label and 50% probability ellipsoids for non-H atoms. Only minor disorder component is shown.
	Fig. 4. The crystal packing of the title compound, viewed down the b axis, showing the molecules stacked down the b axis. Only the major disorder component is shown.

(2-methoxyphenyl)diphenylphosphine top

Crystal data top

C₁₉H₁₇OP	F(000) = 2464
M_r = 292.30	D_x = 1.231 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9973 reflections
a = 31.1813 (8) Å	θ = 2.9–31.4°
b = 7.1474 (2) Å	µ = 0.17 mm⁻¹
c = 28.3025 (8) Å	T = 100 K
β = 90.3795 (12)°	Needle, colourless
V = 6307.5 (3) Å³	0.78 × 0.24 × 0.13 mm
Z = 16

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	11740 independent reflections
Radiation source: fine-focus sealed tube	8873 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
φ and ω scans	θ_max = 33.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −47→47
T_min = 0.879, T_max = 0.978	k = −10→10
49460 measured reflections	l = −42→43

Refinement top

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.0294P)² + 8.0384P] where P = (F_o² + 2F_c²)/3
11740 reflections	(Δ/σ)_max = 0.001
566 parameters	Δρ_max = 0.33 e Å⁻³
157 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₉H₁₇OP	V = 6307.5 (3) Å³
M_r = 292.30	Z = 16
Monoclinic, C2/c	Mo Kα radiation
a = 31.1813 (8) Å	µ = 0.17 mm⁻¹
b = 7.1474 (2) Å	T = 100 K
c = 28.3025 (8) Å	0.78 × 0.24 × 0.13 mm
β = 90.3795 (12)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	11740 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	8873 reflections with I > 2σ(I)
T_min = 0.879, T_max = 0.978	R_int = 0.035
49460 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	157 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.10	Δρ_max = 0.33 e Å⁻³
11740 reflections	Δρ_min = −0.25 e Å⁻³
566 parameters

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 100.0 (1) K.

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
P1A	0.922433 (11)	0.68949 (6)	0.081792 (13)	0.02379 (8)
O1A	0.98898 (3)	0.42835 (19)	0.06278 (4)	0.0356 (3)
C1A	0.89016 (4)	0.5270 (2)	0.04611 (5)	0.0227 (3)
C2A	0.87439 (4)	0.5889 (2)	0.00231 (5)	0.0268 (3)
H2AA	0.8805	0.7097	−0.0078	0.032*
C3A	0.84983 (5)	0.4716 (3)	−0.02601 (5)	0.0311 (3)
H3AA	0.8393	0.5148	−0.0548	0.037*
C4A	0.84080 (5)	0.2902 (3)	−0.01165 (5)	0.0309 (3)
H4AA	0.8245	0.2116	−0.0309	0.037*
C5A	0.85617 (5)	0.2268 (2)	0.03158 (5)	0.0293 (3)
H5AA	0.8501	0.1057	0.0415	0.035*
C6A	0.88069 (4)	0.3442 (2)	0.06009 (5)	0.0256 (3)
H6AA	0.8910	0.3004	0.0890	0.031*
C7A	0.88118 (4)	0.8042 (2)	0.11748 (5)	0.0236 (3)
C8A	0.83846 (5)	0.7462 (2)	0.11895 (5)	0.0274 (3)
H8AA	0.8300	0.6403	0.1023	0.033*
C9A	0.80846 (5)	0.8451 (2)	0.14506 (6)	0.0312 (3)
H9AA	0.7800	0.8065	0.1452	0.037*
C10A	0.82081 (5)	1.0009 (2)	0.17091 (6)	0.0332 (3)
H10A	0.8008	1.0657	0.1888	0.040*
C11A	0.86316 (6)	1.0596 (2)	0.17001 (6)	0.0339 (3)
H11A	0.8716	1.1638	0.1874	0.041*
C12A	0.89293 (5)	0.9637 (2)	0.14327 (5)	0.0291 (3)
H12A	0.9211	1.0057	0.1424	0.035*
C13A	0.94579 (4)	0.5263 (2)	0.12501 (5)	0.0235 (3)
C14A	0.93348 (5)	0.5143 (2)	0.17235 (5)	0.0264 (3)
H14A	0.9118	0.5918	0.1835	0.032*
C15A	0.95316 (5)	0.3878 (2)	0.20307 (5)	0.0317 (3)
H15A	0.9447	0.3811	0.2345	0.038*
C16A	0.98528 (5)	0.2724 (2)	0.18670 (6)	0.0334 (3)
H16A	0.9984	0.1881	0.2072	0.040*
C17A	0.99830 (5)	0.2808 (2)	0.13978 (6)	0.0311 (3)
H17A	1.0199	0.2024	0.1289	0.037*
C18A	0.97864 (4)	0.4080 (2)	0.10933 (5)	0.0277 (3)
C19A	1.01988 (7)	0.3008 (4)	0.04412 (7)	0.0544 (6)
H19A	1.0236	0.3246	0.0110	0.082*
H19B	1.0100	0.1748	0.0485	0.082*
H19C	1.0468	0.3175	0.0603	0.082*
P1B	0.63959 (15)	0.6772 (5)	0.13064 (12)	0.0268 (4)	0.753 (3)
O1B	0.58298 (5)	0.4273 (3)	0.08223 (7)	0.0445 (5)	0.753 (3)
C1B	0.6620 (3)	0.7991 (12)	0.1822 (3)	0.0232 (12)	0.753 (3)
C2B	0.6393 (3)	0.9541 (11)	0.1994 (3)	0.0254 (9)	0.753 (3)
H2BA	0.6142	0.9922	0.1844	0.031*	0.753 (3)
C3B	0.6543 (3)	1.0510 (12)	0.2388 (3)	0.0308 (11)	0.753 (3)
H3BA	0.6386	1.1506	0.2508	0.037*	0.753 (3)
C4B	0.6923 (2)	0.9991 (11)	0.2598 (3)	0.0334 (15)	0.753 (3)
H4BA	0.7029	1.0674	0.2853	0.040*	0.753 (3)
C5B	0.7149 (3)	0.8462 (12)	0.2434 (3)	0.0325 (15)	0.753 (3)
H5BA	0.7404	0.8115	0.2583	0.039*	0.753 (3)
C6B	0.7000 (3)	0.7437 (12)	0.2049 (3)	0.0233 (9)	0.753 (3)
H6BA	0.7151	0.6396	0.1943	0.028*	0.753 (3)
C7B	0.68283 (18)	0.5167 (9)	0.1152 (3)	0.0244 (11)	0.753 (3)
C8B	0.68720 (17)	0.3390 (7)	0.1351 (2)	0.0257 (7)	0.753 (3)
H8BA	0.6667	0.2953	0.1562	0.031*	0.753 (3)
C9B	0.7221 (2)	0.2265 (10)	0.1235 (3)	0.0352 (14)	0.753 (3)
H9BA	0.7247	0.1077	0.1366	0.042*	0.753 (3)
C10B	0.7534 (2)	0.2906 (9)	0.0922 (3)	0.0375 (14)	0.753 (3)
H10B	0.7765	0.2152	0.0844	0.045*	0.753 (3)
C11B	0.7493 (2)	0.4669 (8)	0.0733 (3)	0.0383 (12)	0.753 (3)
H11B	0.7703	0.5117	0.0530	0.046*	0.753 (3)
C12B	0.71416 (17)	0.5798 (9)	0.0841 (3)	0.0337 (13)	0.753 (3)
H12B	0.7116	0.6977	0.0705	0.040*	0.753 (3)
C13B	0.60176 (18)	0.5166 (9)	0.16012 (18)	0.0257 (9)	0.753 (3)
C14B	0.5956 (2)	0.4999 (9)	0.20859 (17)	0.0304 (10)	0.753 (3)
H14B	0.6130	0.5685	0.2291	0.037*	0.753 (3)
C15B	0.56431 (18)	0.3837 (8)	0.22724 (15)	0.0410 (10)	0.753 (3)
H15B	0.5598	0.3795	0.2597	0.049*	0.753 (3)
C16B	0.54009 (16)	0.2750 (8)	0.19734 (18)	0.0511 (12)	0.753 (3)
H16B	0.5197	0.1945	0.2099	0.061*	0.753 (3)
C17B	0.54545 (16)	0.2829 (8)	0.14911 (18)	0.0481 (12)	0.753 (3)
H17B	0.5290	0.2073	0.1293	0.058*	0.753 (3)
C18B	0.5757 (2)	0.4047 (11)	0.13005 (18)	0.0381 (11)	0.753 (3)
C19B	0.55769 (8)	0.3189 (5)	0.04961 (13)	0.0667 (11)	0.753 (3)
H19D	0.5654	0.3508	0.0178	0.100*	0.753 (3)
H19E	0.5278	0.3453	0.0543	0.100*	0.753 (3)
H19F	0.5629	0.1882	0.0549	0.100*	0.753 (3)
P1C	0.6453 (5)	0.6726 (14)	0.1308 (4)	0.0283 (15)	0.247 (3)
O1C	0.72148 (13)	0.7423 (6)	0.07269 (15)	0.0252 (10)	0.247 (3)
C1C	0.6668 (8)	0.781 (3)	0.1856 (8)	0.018 (2)	0.247 (3)
C2C	0.6454 (9)	0.937 (4)	0.2032 (10)	0.030 (3)	0.247 (3)
H2CA	0.6199	0.9740	0.1888	0.037*	0.247 (3)
C3C	0.6608 (8)	1.040 (4)	0.2415 (10)	0.031 (4)	0.247 (3)
H3CA	0.6463	1.1472	0.2509	0.037*	0.247 (3)
C4C	0.6969 (6)	0.985 (3)	0.2652 (7)	0.022 (2)	0.247 (3)
H4CA	0.7053	1.0434	0.2931	0.027*	0.247 (3)
C5C	0.7207 (7)	0.839 (3)	0.2466 (8)	0.017 (2)	0.247 (3)
H5CA	0.7469	0.8069	0.2602	0.021*	0.247 (3)
C6C	0.7054 (9)	0.741 (4)	0.2080 (11)	0.029 (3)	0.247 (3)
H6CA	0.7220	0.6432	0.1963	0.035*	0.247 (3)
C7C	0.6038 (7)	0.515 (3)	0.1504 (5)	0.027 (3)	0.247 (3)
C8C	0.5923 (5)	0.512 (2)	0.1981 (4)	0.0179 (18)	0.247 (3)
H8CA	0.6050	0.5937	0.2195	0.022*	0.247 (3)
C9C	0.5611 (6)	0.381 (3)	0.2131 (3)	0.027 (2)	0.247 (3)
H9CA	0.5552	0.3687	0.2451	0.032*	0.247 (3)
C10C	0.5388 (5)	0.270 (2)	0.1800 (3)	0.027 (2)	0.247 (3)
H10C	0.5174	0.1875	0.1895	0.033*	0.247 (3)
C11C	0.5496 (5)	0.286 (3)	0.1329 (3)	0.029 (2)	0.247 (3)
H11C	0.5348	0.2158	0.1105	0.035*	0.247 (3)
C12C	0.5818 (6)	0.404 (3)	0.1183 (4)	0.026 (3)	0.247 (3)
H12C	0.5888	0.4101	0.0864	0.031*	0.247 (3)
C13C	0.6904 (5)	0.507 (3)	0.1199 (8)	0.020 (2)	0.247 (3)
C14C	0.6915 (6)	0.321 (3)	0.1361 (9)	0.0304 (10)	0.247 (3)
H14C	0.6696	0.2816	0.1560	0.037*	0.247 (3)
C15C	0.7225 (6)	0.196 (3)	0.1247 (8)	0.019 (2)	0.247 (3)
H15C	0.7226	0.0753	0.1372	0.023*	0.247 (3)
C16C	0.7535 (7)	0.254 (3)	0.0939 (9)	0.024 (2)	0.247 (3)
H16C	0.7755	0.1715	0.0863	0.029*	0.247 (3)
C17C	0.7538 (6)	0.428 (2)	0.0736 (6)	0.024 (2)	0.247 (3)
H17C	0.7740	0.4585	0.0509	0.028*	0.247 (3)
C18C	0.7232 (5)	0.559 (2)	0.0877 (6)	0.020 (2)	0.247 (3)
C19C	0.74898 (19)	0.7931 (10)	0.0343 (2)	0.0293 (14)	0.247 (3)
H19I	0.7424	0.9182	0.0243	0.044*	0.247 (3)
H19G	0.7445	0.7082	0.0085	0.044*	0.247 (3)
H19H	0.7784	0.7868	0.0446	0.044*	0.247 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1A	0.01805 (15)	0.02824 (19)	0.02511 (16)	−0.00272 (14)	0.00114 (12)	0.00586 (15)
O1A	0.0244 (5)	0.0477 (7)	0.0347 (6)	0.0082 (5)	0.0081 (4)	0.0068 (5)
C1A	0.0180 (5)	0.0287 (7)	0.0215 (6)	0.0011 (5)	0.0010 (4)	0.0040 (5)
C2A	0.0230 (6)	0.0322 (8)	0.0252 (6)	0.0035 (6)	0.0004 (5)	0.0077 (6)
C3A	0.0278 (7)	0.0425 (9)	0.0229 (6)	0.0034 (7)	−0.0034 (5)	0.0055 (6)
C4A	0.0262 (7)	0.0401 (9)	0.0262 (7)	−0.0003 (6)	−0.0044 (5)	−0.0028 (6)
C5A	0.0270 (7)	0.0302 (8)	0.0306 (7)	−0.0014 (6)	−0.0019 (6)	0.0034 (6)
C6A	0.0235 (6)	0.0307 (8)	0.0226 (6)	−0.0021 (6)	−0.0015 (5)	0.0066 (6)
C7A	0.0225 (6)	0.0234 (7)	0.0249 (6)	−0.0013 (5)	−0.0005 (5)	0.0064 (5)
C8A	0.0232 (6)	0.0263 (7)	0.0328 (7)	−0.0021 (6)	0.0020 (5)	0.0013 (6)
C9A	0.0234 (6)	0.0319 (8)	0.0383 (8)	0.0021 (6)	0.0034 (6)	0.0018 (7)
C10A	0.0380 (8)	0.0301 (8)	0.0316 (7)	0.0074 (7)	0.0036 (6)	0.0020 (7)
C11A	0.0442 (9)	0.0266 (8)	0.0309 (7)	−0.0016 (7)	−0.0037 (6)	−0.0006 (6)
C12A	0.0295 (7)	0.0279 (8)	0.0298 (7)	−0.0060 (6)	−0.0024 (6)	0.0047 (6)
C13A	0.0164 (5)	0.0286 (7)	0.0255 (6)	−0.0030 (5)	−0.0027 (5)	0.0019 (6)
C14A	0.0254 (6)	0.0279 (7)	0.0258 (6)	−0.0020 (6)	−0.0027 (5)	0.0003 (6)
C15A	0.0383 (8)	0.0308 (8)	0.0260 (7)	−0.0020 (7)	−0.0085 (6)	0.0020 (6)
C16A	0.0359 (8)	0.0296 (8)	0.0345 (8)	−0.0017 (7)	−0.0158 (6)	0.0035 (7)
C17A	0.0220 (6)	0.0319 (8)	0.0395 (8)	0.0017 (6)	−0.0063 (6)	0.0006 (7)
C18A	0.0172 (6)	0.0338 (8)	0.0320 (7)	−0.0028 (6)	−0.0019 (5)	0.0024 (6)
C19A	0.0431 (10)	0.0717 (16)	0.0486 (11)	0.0230 (11)	0.0186 (8)	0.0086 (11)
P1B	0.0223 (7)	0.0251 (6)	0.0331 (7)	−0.0009 (4)	−0.0026 (4)	0.0016 (5)
O1B	0.0230 (7)	0.0508 (11)	0.0596 (12)	−0.0003 (7)	−0.0055 (7)	−0.0228 (9)
C1B	0.0171 (14)	0.019 (2)	0.033 (2)	0.0003 (12)	0.0018 (11)	0.0087 (14)
C2B	0.022 (3)	0.0197 (15)	0.0346 (18)	0.0056 (14)	0.0058 (14)	0.0072 (15)
C3B	0.032 (3)	0.0228 (18)	0.0381 (19)	0.0035 (15)	0.0141 (16)	0.0051 (14)
C4B	0.042 (3)	0.0262 (19)	0.032 (2)	−0.0050 (17)	0.0038 (16)	−0.0053 (18)
C5B	0.024 (3)	0.037 (2)	0.036 (2)	−0.0034 (16)	−0.0011 (16)	0.0020 (16)
C6B	0.020 (2)	0.0192 (17)	0.0303 (19)	−0.0017 (14)	0.0025 (14)	−0.0032 (15)
C7B	0.0172 (18)	0.0297 (15)	0.026 (2)	−0.0052 (12)	−0.0023 (17)	−0.0002 (12)
C8B	0.0198 (15)	0.0315 (17)	0.0257 (11)	0.0019 (10)	0.0014 (11)	−0.0023 (12)
C9B	0.033 (2)	0.032 (3)	0.040 (3)	0.0024 (16)	−0.0053 (16)	−0.0005 (18)
C10B	0.0193 (15)	0.048 (4)	0.045 (3)	0.000 (2)	0.0028 (14)	−0.012 (2)
C11B	0.0277 (19)	0.040 (3)	0.047 (2)	−0.0135 (18)	0.0116 (15)	−0.0087 (19)
C12B	0.029 (2)	0.0335 (19)	0.038 (2)	−0.0073 (14)	0.0024 (18)	−0.0023 (15)
C13B	0.0163 (11)	0.0194 (13)	0.042 (3)	−0.0016 (9)	0.0003 (16)	0.0011 (18)
C14B	0.0233 (15)	0.0258 (14)	0.042 (2)	0.0020 (11)	−0.0002 (15)	0.0160 (17)
C15B	0.0272 (16)	0.0299 (16)	0.066 (3)	0.0030 (12)	0.017 (2)	0.016 (2)
C16B	0.0222 (15)	0.0285 (16)	0.103 (4)	−0.0010 (12)	0.017 (2)	0.009 (3)
C17B	0.0208 (12)	0.0288 (17)	0.095 (4)	−0.0038 (10)	0.003 (3)	−0.009 (4)
C18B	0.0203 (16)	0.0334 (18)	0.061 (3)	0.0038 (12)	0.000 (2)	−0.010 (2)
C19B	0.0240 (11)	0.079 (2)	0.097 (2)	0.0046 (13)	−0.0092 (13)	−0.057 (2)
P1C	0.031 (4)	0.0269 (19)	0.0274 (18)	−0.0050 (17)	−0.0063 (16)	0.0141 (16)
O1C	0.025 (2)	0.024 (2)	0.027 (2)	−0.0006 (16)	0.0063 (15)	0.0068 (17)
C1C	0.026 (7)	0.008 (4)	0.019 (4)	0.000 (4)	0.005 (4)	0.001 (4)
C2C	0.014 (5)	0.033 (7)	0.043 (5)	0.011 (3)	−0.001 (3)	0.017 (4)
C3C	0.027 (6)	0.021 (6)	0.044 (7)	0.004 (4)	0.009 (4)	−0.012 (5)
C4C	0.013 (3)	0.030 (5)	0.024 (4)	−0.003 (3)	0.005 (3)	0.008 (3)
C5C	0.012 (4)	0.012 (4)	0.028 (5)	0.000 (3)	−0.001 (3)	−0.009 (3)
C6C	0.012 (4)	0.037 (7)	0.039 (6)	0.004 (4)	−0.007 (3)	0.006 (4)
C7C	0.032 (5)	0.038 (5)	0.013 (4)	0.004 (3)	0.004 (3)	0.004 (3)
C8C	0.012 (3)	0.019 (4)	0.023 (4)	0.001 (2)	−0.004 (3)	0.013 (3)
C9C	0.028 (4)	0.033 (4)	0.019 (3)	0.002 (3)	0.001 (3)	0.007 (4)
C10C	0.022 (4)	0.027 (4)	0.034 (4)	−0.009 (3)	−0.002 (4)	0.003 (5)
C11C	0.034 (6)	0.031 (4)	0.022 (3)	−0.004 (4)	−0.002 (3)	0.000 (4)
C12C	0.026 (6)	0.023 (4)	0.029 (5)	−0.009 (4)	0.005 (3)	−0.003 (4)
C13C	0.017 (5)	0.023 (4)	0.019 (4)	−0.001 (3)	−0.009 (4)	−0.004 (3)
C14C	0.0233 (15)	0.0258 (14)	0.042 (2)	0.0020 (11)	−0.0002 (15)	0.0160 (17)
C15C	0.012 (4)	0.023 (5)	0.023 (5)	0.001 (3)	0.009 (3)	0.008 (4)
C16C	0.030 (5)	0.017 (4)	0.025 (5)	−0.006 (3)	−0.001 (3)	0.005 (4)
C17C	0.030 (5)	0.025 (5)	0.016 (3)	−0.001 (3)	0.006 (3)	0.000 (3)
C18C	0.024 (5)	0.020 (4)	0.017 (3)	−0.011 (3)	−0.002 (4)	0.006 (3)
C19C	0.026 (3)	0.035 (3)	0.026 (3)	0.001 (2)	0.005 (2)	0.010 (2)

Geometric parameters (Å, º) top

P1A—C7A	1.8343 (15)	C9B—C10B	1.396 (7)
P1A—C1A	1.8351 (15)	C9B—H9BA	0.9300
P1A—C13A	1.8370 (15)	C10B—C11B	1.375 (6)
O1A—C18A	1.3661 (18)	C10B—H10B	0.9300
O1A—C19A	1.430 (2)	C11B—C12B	1.397 (6)
C1A—C6A	1.397 (2)	C11B—H11B	0.9300
C1A—C2A	1.4021 (19)	C12B—H12B	0.9300
C2A—C3A	1.387 (2)	C13B—C14B	1.392 (6)
C2A—H2AA	0.9300	C13B—C18B	1.418 (6)
C3A—C4A	1.389 (2)	C14B—C15B	1.389 (6)
C3A—H3AA	0.9300	C14B—H14B	0.9300
C4A—C5A	1.387 (2)	C15B—C16B	1.372 (6)
C4A—H4AA	0.9300	C15B—H15B	0.9300
C5A—C6A	1.390 (2)	C16B—C17B	1.378 (6)
C5A—H5AA	0.9300	C16B—H16B	0.9300
C6A—H6AA	0.9300	C17B—C18B	1.396 (6)
C7A—C8A	1.3957 (19)	C17B—H17B	0.9300
C7A—C12A	1.401 (2)	C19B—H19D	0.9600
C8A—C9A	1.389 (2)	C19B—H19E	0.9600
C8A—H8AA	0.9300	C19B—H19F	0.9600
C9A—C10A	1.386 (2)	P1C—C7C	1.807 (15)
C9A—H9AA	0.9300	P1C—C1C	1.855 (12)
C10A—C11A	1.386 (2)	P1C—C13C	1.864 (15)
C10A—H10A	0.9300	O1C—C18C	1.381 (13)
C11A—C12A	1.383 (2)	O1C—C19C	1.434 (7)
C11A—H11A	0.9300	C1C—C6C	1.386 (14)
C12A—H12A	0.9300	C1C—C2C	1.394 (13)
C13A—C14A	1.399 (2)	C2C—C3C	1.390 (14)
C13A—C18A	1.403 (2)	C2C—H2CA	0.9300
C14A—C15A	1.394 (2)	C3C—C4C	1.367 (14)
C14A—H14A	0.9300	C3C—H3CA	0.9300
C15A—C16A	1.380 (2)	C4C—C5C	1.385 (13)
C15A—H15A	0.9300	C4C—H4CA	0.9300
C16A—C17A	1.392 (2)	C5C—C6C	1.381 (14)
C16A—H16A	0.9300	C5C—H5CA	0.9300
C17A—C18A	1.392 (2)	C6C—H6CA	0.9300
C17A—H17A	0.9300	C7C—C12C	1.382 (16)
C19A—H19A	0.9600	C7C—C8C	1.399 (14)
C19A—H19B	0.9600	C8C—C9C	1.416 (16)
C19A—H19C	0.9600	C8C—H8CA	0.9300
P1B—C7B	1.825 (6)	C9C—C10C	1.410 (13)
P1B—C1B	1.834 (5)	C9C—H9CA	0.9300
P1B—C13B	1.849 (5)	C10C—C11C	1.382 (10)
O1B—C18B	1.383 (5)	C10C—H10C	0.9300
O1B—C19B	1.437 (3)	C11C—C12C	1.376 (14)
C1B—C6B	1.402 (5)	C11C—H11C	0.9300
C1B—C2B	1.403 (5)	C12C—H12C	0.9300
C2B—C3B	1.389 (5)	C13C—C14C	1.407 (17)
C2B—H2BA	0.9300	C13C—C18C	1.424 (16)
C3B—C4B	1.375 (6)	C14C—C15C	1.359 (17)
C3B—H3BA	0.9300	C14C—H14C	0.9300
C4B—C5B	1.383 (6)	C15C—C16C	1.373 (16)
C4B—H4BA	0.9300	C15C—H15C	0.9300
C5B—C6B	1.392 (5)	C16C—C17C	1.368 (15)
C5B—H5BA	0.9300	C16C—H16C	0.9300
C6B—H6BA	0.9300	C17C—C18C	1.393 (14)
C7B—C12B	1.395 (7)	C17C—H17C	0.9300
C7B—C8B	1.396 (6)	C19C—H19I	0.9600
C8B—C9B	1.395 (6)	C19C—H19G	0.9600
C8B—H8BA	0.9300	C19C—H19H	0.9600

C7A—P1A—C1A	101.65 (6)	C8B—C9B—H9BA	119.7
C7A—P1A—C13A	101.15 (6)	C10B—C9B—H9BA	119.7
C1A—P1A—C13A	100.27 (7)	C11B—C10B—C9B	119.0 (6)
C18A—O1A—C19A	116.89 (14)	C11B—C10B—H10B	120.5
C6A—C1A—C2A	118.15 (13)	C9B—C10B—H10B	120.5
C6A—C1A—P1A	123.50 (10)	C10B—C11B—C12B	121.0 (5)
C2A—C1A—P1A	118.35 (12)	C10B—C11B—H11B	119.5
C3A—C2A—C1A	120.62 (15)	C12B—C11B—H11B	119.5
C3A—C2A—H2AA	119.7	C7B—C12B—C11B	120.3 (5)
C1A—C2A—H2AA	119.7	C7B—C12B—H12B	119.8
C2A—C3A—C4A	120.51 (14)	C11B—C12B—H12B	119.8
C2A—C3A—H3AA	119.7	C14B—C13B—C18B	117.5 (4)
C4A—C3A—H3AA	119.7	C14B—C13B—P1B	126.2 (4)
C5A—C4A—C3A	119.58 (15)	C18B—C13B—P1B	116.3 (4)
C5A—C4A—H4AA	120.2	C15B—C14B—C13B	121.8 (5)
C3A—C4A—H4AA	120.2	C15B—C14B—H14B	119.1
C4A—C5A—C6A	120.03 (15)	C13B—C14B—H14B	119.1
C4A—C5A—H5AA	120.0	C16B—C15B—C14B	119.3 (4)
C6A—C5A—H5AA	120.0	C16B—C15B—H15B	120.3
C5A—C6A—C1A	121.11 (13)	C14B—C15B—H15B	120.3
C5A—C6A—H6AA	119.4	C15B—C16B—C17B	121.2 (4)
C1A—C6A—H6AA	119.4	C15B—C16B—H16B	119.4
C8A—C7A—C12A	118.18 (14)	C17B—C16B—H16B	119.4
C8A—C7A—P1A	123.82 (12)	C16B—C17B—C18B	119.7 (4)
C12A—C7A—P1A	117.94 (11)	C16B—C17B—H17B	120.2
C9A—C8A—C7A	120.74 (15)	C18B—C17B—H17B	120.2
C9A—C8A—H8AA	119.6	O1B—C18B—C17B	124.5 (4)
C7A—C8A—H8AA	119.6	O1B—C18B—C13B	115.2 (4)
C10A—C9A—C8A	120.25 (15)	C17B—C18B—C13B	120.4 (4)
C10A—C9A—H9AA	119.9	C7C—P1C—C1C	105.1 (12)
C8A—C9A—H9AA	119.9	C7C—P1C—C13C	101.4 (10)
C9A—C10A—C11A	119.68 (15)	C1C—P1C—C13C	97.7 (10)
C9A—C10A—H10A	120.2	C18C—O1C—C19C	116.7 (7)
C11A—C10A—H10A	120.2	C6C—C1C—C2C	114.7 (12)
C12A—C11A—C10A	120.18 (15)	C6C—C1C—P1C	127.2 (13)
C12A—C11A—H11A	119.9	C2C—C1C—P1C	117.5 (13)
C10A—C11A—H11A	119.9	C3C—C2C—C1C	122.6 (14)
C11A—C12A—C7A	120.94 (14)	C3C—C2C—H2CA	118.7
C11A—C12A—H12A	119.5	C1C—C2C—H2CA	118.7
C7A—C12A—H12A	119.5	C4C—C3C—C2C	120.6 (15)
C14A—C13A—C18A	118.12 (13)	C4C—C3C—H3CA	119.7
C14A—C13A—P1A	124.53 (11)	C2C—C3C—H3CA	119.7
C18A—C13A—P1A	117.34 (11)	C3C—C4C—C5C	118.1 (15)
C15A—C14A—C13A	121.01 (15)	C3C—C4C—H4CA	120.9
C15A—C14A—H14A	119.5	C5C—C4C—H4CA	120.9
C13A—C14A—H14A	119.5	C6C—C5C—C4C	120.1 (16)
C16A—C15A—C14A	119.70 (15)	C6C—C5C—H5CA	120.0
C16A—C15A—H15A	120.2	C4C—C5C—H5CA	120.0
C14A—C15A—H15A	120.2	C5C—C6C—C1C	123.4 (16)
C15A—C16A—C17A	120.77 (14)	C5C—C6C—H6CA	118.3
C15A—C16A—H16A	119.6	C1C—C6C—H6CA	118.3
C17A—C16A—H16A	119.6	C12C—C7C—C8C	119.7 (12)
C18A—C17A—C16A	119.24 (15)	C12C—C7C—P1C	120.6 (10)
C18A—C17A—H17A	120.4	C8C—C7C—P1C	119.6 (11)
C16A—C17A—H17A	120.4	C7C—C8C—C9C	118.7 (12)
O1A—C18A—C17A	124.11 (14)	C7C—C8C—H8CA	120.6
O1A—C18A—C13A	114.73 (13)	C9C—C8C—H8CA	120.6
C17A—C18A—C13A	121.16 (14)	C10C—C9C—C8C	120.7 (10)
O1A—C19A—H19A	109.5	C10C—C9C—H9CA	119.7
O1A—C19A—H19B	109.5	C8C—C9C—H9CA	119.7
H19A—C19A—H19B	109.5	C11C—C10C—C9C	118.0 (11)
O1A—C19A—H19C	109.5	C11C—C10C—H10C	121.0
H19A—C19A—H19C	109.5	C9C—C10C—H10C	121.0
H19B—C19A—H19C	109.5	C12C—C11C—C10C	121.8 (12)
C7B—P1B—C1B	102.2 (4)	C12C—C11C—H11C	119.1
C7B—P1B—C13B	101.1 (3)	C10C—C11C—H11C	119.1
C1B—P1B—C13B	100.2 (4)	C11C—C12C—C7C	120.8 (11)
C18B—O1B—C19B	118.3 (3)	C11C—C12C—H12C	119.6
C6B—C1B—C2B	119.4 (4)	C7C—C12C—H12C	119.6
C6B—C1B—P1B	123.1 (4)	C14C—C13C—C18C	115.9 (13)
C2B—C1B—P1B	117.5 (4)	C14C—C13C—P1C	124.2 (12)
C3B—C2B—C1B	120.3 (5)	C18C—C13C—P1C	119.3 (12)
C3B—C2B—H2BA	119.8	C15C—C14C—C13C	124.2 (16)
C1B—C2B—H2BA	119.8	C15C—C14C—H14C	117.9
C4B—C3B—C2B	119.8 (5)	C13C—C14C—H14C	117.9
C4B—C3B—H3BA	120.1	C14C—C15C—C16C	117.1 (16)
C2B—C3B—H3BA	120.1	C14C—C15C—H15C	121.4
C3B—C4B—C5B	120.6 (5)	C16C—C15C—H15C	121.4
C3B—C4B—H4BA	119.7	C17C—C16C—C15C	123.2 (17)
C5B—C4B—H4BA	119.7	C17C—C16C—H16C	118.4
C4B—C5B—C6B	120.7 (5)	C15C—C16C—H16C	118.4
C4B—C5B—H5BA	119.7	C16C—C17C—C18C	119.0 (14)
C6B—C5B—H5BA	119.7	C16C—C17C—H17C	120.5
C5B—C6B—C1B	119.2 (5)	C18C—C17C—H17C	120.5
C5B—C6B—H6BA	120.4	O1C—C18C—C17C	125.1 (12)
C1B—C6B—H6BA	120.4	O1C—C18C—C13C	114.5 (11)
C12B—C7B—C8B	118.8 (5)	C17C—C18C—C13C	120.4 (12)
C12B—C7B—P1B	118.0 (4)	O1C—C19C—H19I	109.5
C8B—C7B—P1B	123.1 (4)	O1C—C19C—H19G	109.5
C9B—C8B—C7B	120.2 (5)	H19I—C19C—H19G	109.5
C9B—C8B—H8BA	119.9	O1C—C19C—H19H	109.5
C7B—C8B—H8BA	119.9	H19I—C19C—H19H	109.5
C8B—C9B—C10B	120.6 (6)	H19G—C19C—H19H	109.5

C7A—P1A—C1A—C6A	−90.02 (13)	C8B—C7B—C12B—C11B	−0.3 (12)
C13A—P1A—C1A—C6A	13.75 (13)	P1B—C7B—C12B—C11B	176.2 (6)
C7A—P1A—C1A—C2A	90.47 (12)	C10B—C11B—C12B—C7B	1.4 (12)
C13A—P1A—C1A—C2A	−165.76 (11)	C7B—P1B—C13B—C14B	102.8 (7)
C6A—C1A—C2A—C3A	0.5 (2)	C1B—P1B—C13B—C14B	−1.9 (7)
P1A—C1A—C2A—C3A	−179.99 (11)	C7B—P1B—C13B—C18B	−79.4 (7)
C1A—C2A—C3A—C4A	−0.6 (2)	C1B—P1B—C13B—C18B	175.9 (6)
C2A—C3A—C4A—C5A	0.6 (2)	C18B—C13B—C14B—C15B	−2.2 (10)
C3A—C4A—C5A—C6A	−0.4 (2)	P1B—C13B—C14B—C15B	175.6 (6)
C4A—C5A—C6A—C1A	0.3 (2)	C13B—C14B—C15B—C16B	3.3 (10)
C2A—C1A—C6A—C5A	−0.3 (2)	C14B—C15B—C16B—C17B	−1.8 (9)
P1A—C1A—C6A—C5A	−179.81 (11)	C15B—C16B—C17B—C18B	−0.7 (9)
C1A—P1A—C7A—C8A	8.97 (14)	C19B—O1B—C18B—C17B	0.2 (9)
C13A—P1A—C7A—C8A	−94.10 (13)	C19B—O1B—C18B—C13B	−179.8 (5)
C1A—P1A—C7A—C12A	−168.38 (11)	C16B—C17B—C18B—O1B	−178.3 (6)
C13A—P1A—C7A—C12A	88.55 (12)	C16B—C17B—C18B—C13B	1.7 (11)
C12A—C7A—C8A—C9A	0.4 (2)	C14B—C13B—C18B—O1B	179.7 (6)
P1A—C7A—C8A—C9A	−176.94 (12)	P1B—C13B—C18B—O1B	1.6 (9)
C7A—C8A—C9A—C10A	−1.4 (2)	C14B—C13B—C18B—C17B	−0.3 (11)
C8A—C9A—C10A—C11A	1.0 (2)	P1B—C13B—C18B—C17B	−178.3 (6)
C9A—C10A—C11A—C12A	0.3 (2)	C7C—P1C—C1C—C6C	105 (3)
C10A—C11A—C12A—C7A	−1.3 (2)	C13C—P1C—C1C—C6C	1 (4)
C8A—C7A—C12A—C11A	0.9 (2)	C7C—P1C—C1C—C2C	−85 (3)
P1A—C7A—C12A—C11A	178.43 (12)	C13C—P1C—C1C—C2C	171 (3)
C7A—P1A—C13A—C14A	−2.63 (14)	C6C—C1C—C2C—C3C	−3 (6)
C1A—P1A—C13A—C14A	−106.80 (13)	P1C—C1C—C2C—C3C	−174 (3)
C7A—P1A—C13A—C18A	178.33 (11)	C1C—C2C—C3C—C4C	−4 (6)
C1A—P1A—C13A—C18A	74.16 (12)	C2C—C3C—C4C—C5C	8 (5)
C18A—C13A—C14A—C15A	−0.3 (2)	C3C—C4C—C5C—C6C	−7 (4)
P1A—C13A—C14A—C15A	−179.29 (12)	C4C—C5C—C6C—C1C	0 (6)
C13A—C14A—C15A—C16A	0.0 (2)	C2C—C1C—C6C—C5C	4 (6)
C14A—C15A—C16A—C17A	0.0 (2)	P1C—C1C—C6C—C5C	175 (3)
C15A—C16A—C17A—C18A	0.3 (2)	C1C—P1C—C7C—C12C	−178 (2)
C19A—O1A—C18A—C17A	4.5 (2)	C13C—P1C—C7C—C12C	−76 (2)
C19A—O1A—C18A—C13A	−175.18 (16)	C1C—P1C—C7C—C8C	6 (2)
C16A—C17A—C18A—O1A	179.78 (15)	C13C—P1C—C7C—C8C	107 (2)
C16A—C17A—C18A—C13A	−0.5 (2)	C12C—C7C—C8C—C9C	6 (3)
C14A—C13A—C18A—O1A	−179.75 (13)	P1C—C7C—C8C—C9C	−177.2 (17)
P1A—C13A—C18A—O1A	−0.65 (17)	C7C—C8C—C9C—C10C	−6 (3)
C14A—C13A—C18A—C17A	0.5 (2)	C8C—C9C—C10C—C11C	3 (3)
P1A—C13A—C18A—C17A	179.62 (12)	C9C—C10C—C11C—C12C	1 (3)
C7B—P1B—C1B—C6B	−9.5 (11)	C10C—C11C—C12C—C7C	−2 (4)
C13B—P1B—C1B—C6B	94.3 (10)	C8C—C7C—C12C—C11C	−2 (4)
C7B—P1B—C1B—C2B	170.9 (9)	P1C—C7C—C12C—C11C	−178.9 (19)
C13B—P1B—C1B—C2B	−85.3 (10)	C7C—P1C—C13C—C14C	−15 (2)
C6B—C1B—C2B—C3B	−0.5 (18)	C1C—P1C—C13C—C14C	93 (2)
P1B—C1B—C2B—C3B	179.1 (9)	C7C—P1C—C13C—C18C	156.0 (17)
C1B—C2B—C3B—C4B	2.5 (17)	C1C—P1C—C13C—C18C	−97 (2)
C2B—C3B—C4B—C5B	−2.8 (15)	C18C—C13C—C14C—C15C	3 (4)
C3B—C4B—C5B—C6B	1.0 (16)	P1C—C13C—C14C—C15C	174 (2)
C4B—C5B—C6B—C1B	1.1 (17)	C13C—C14C—C15C—C16C	−3 (4)
C2B—C1B—C6B—C5B	−1.3 (17)	C14C—C15C—C16C—C17C	−2 (4)
P1B—C1B—C6B—C5B	179.1 (9)	C15C—C16C—C17C—C18C	6 (4)
C1B—P1B—C7B—C12B	−89.0 (7)	C19C—O1C—C18C—C17C	10 (2)
C13B—P1B—C7B—C12B	167.9 (6)	C19C—O1C—C18C—C13C	−169.5 (14)
C1B—P1B—C7B—C8B	87.3 (8)	C16C—C17C—C18C—O1C	175 (2)
C13B—P1B—C7B—C8B	−15.8 (7)	C16C—C17C—C18C—C13C	−5 (3)
C12B—C7B—C8B—C9B	−0.7 (12)	C14C—C13C—C18C—O1C	−179.5 (19)
P1B—C7B—C8B—C9B	−177.0 (7)	P1C—C13C—C18C—O1C	9 (2)
C7B—C8B—C9B—C10B	0.7 (14)	C14C—C13C—C18C—C17C	1 (3)
C8B—C9B—C10B—C11B	0.4 (15)	P1C—C13C—C18C—C17C	−170.6 (17)
C9B—C10B—C11B—C12B	−1.4 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4A—H4AA···Cg1ⁱ	0.93	2.65	3.520 (9)	156
C4A—H4AA···Cg2ⁱ	0.93	2.58	3.471 (3)	159
C17A—H17A···Cg3ⁱⁱ	0.93	2.91	3.645 (8)	137
C10C—H10C···Cg4ⁱⁱ	0.93	2.78	3.561 (15)	142

Symmetry codes: (i) −x+3/2, −y+1/2, −z; (ii) −x−1, −y−1, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇OP
M_r	292.30
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	31.1813 (8), 7.1474 (2), 28.3025 (8)
β (°)	90.3795 (12)
V (Å³)	6307.5 (3)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.78 × 0.24 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.879, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	49460, 11740, 8873
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.765

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.123, 1.10
No. of reflections	11740
No. of parameters	566
No. of restraints	157
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.25

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4A—H4AA···Cg1ⁱ	0.9300	2.65	3.520 (9)	156
C4A—H4AA···Cg2ⁱ	0.9300	2.58	3.471 (3)	159
C17A—H17A···Cg3ⁱⁱ	0.9300	2.91	3.645 (8)	137
C10C—H10C···Cg4ⁱⁱ	0.9300	2.78	3.561 (15)	142

Symmetry codes: (i) −x+3/2, −y+1/2, −z; (ii) −x−1, −y−1, −z.

Footnotes

‡On secondment to: Multimedia University, Melaka Campus, Jalan Ayer Keroh Lama, 74750 Melaka, Malaysia.

§Thomson Reuters ResearcherID: A-5523-2009.

¶Thomson Reuters ResearcherID: A-3561-2009. Additional correspondence author, e-mail: hkfun@usm.com.

Acknowledgements

The authors would like to thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research grant No. 1001/PJJAUH/811115. HKF thanks USM for the Research University Golden Goose grant No. 1001/PFIZIK/811012. CSY thanks USM for the award of a USM Fellowship.

References

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