(6,6′-Dimeth­oxy­biphenyl-2,2′-di­yl)bis(diphenyl­phosphane) P,P′-dioxide dihydrate

Dai, D.; Tang, L.; Gong, Y.

doi:10.1107/S1600536812005314

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o804

doi:10.1107/S1600536812005314

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(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphane) P,P′-dioxide dihydrate

Dongmei Dai,^a Lin Tang ^b and Yanqing Gong ^c ^*

^aKey Laboratory for Molecular Design and Nutrition Engineering, Ningbo Institute of Technology, Zhejiang University, Ningbo 315104, People's Republic of China, ^bZhejiang Pharmaceutical College, Ningbo 315100, People's Republic of China, and ^cState Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, CAS, 345 Lingling Road, Shanghai 200032, People's Republic of People's Republic of China
^*Correspondence e-mail: gongyanqing@sioc.ac.cn

(Received 14 December 2011; accepted 7 February 2012; online 24 February 2012)

In the title compound, C₃₈H₃₂O₄P₂·2H₂O, the dihedral angle between the methoxyphenol rings is 84.11 (7)°. O—H⋯O hydrogen bonds connect the water molecules of crystallization with the main molecule.

Related literature

For the synthesis of the title compound and its unsolvated crystal structure, see: Doherty et al. (2009 ). For similar structures, see: Meijboom (2011 ); Wang et al. (2011 ); Warsink et al. (2011 ).

Experimental

Crystal data

C₃₈H₃₂O₄P₂·2H₂O
M_r = 650.61
Orthorhombic, P b c a
a = 13.108 (3) Å
b = 15.650 (3) Å
c = 33.967 (7) Å
V = 6968 (3) Å³
Z = 8
Cu Kα radiation
μ = 1.50 mm⁻¹
T = 296 K
0.23 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.725, T_max = 0.865
31453 measured reflections
6197 independent reflections
4670 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.130
S = 1.03
6197 reflections
415 parameters
3 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1′—H1′A⋯O4	0.85	2.31	2.854 (4)	123
O2′—H2′A⋯O3	0.85	1.96	2.799 (3)	169

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812005314/hb6568sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812005314/hb6568Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812005314/hb6568Isup3.cml

checkCIF report

Comment top

The title compound, (I) (Fig. 1), (6,6'-Dimethoxybiphenyl-2,2'-diyl)- bis(diphenylphosphine)dioxide dihydrate can be synthesized according to the procedure of Doherty et al., (2009).

Compared with the structure of C₃₈H₃₂O₄P₂ (CCDC 756817), Doherty et al., (2009), in which weak intermolecular C—H···O hydrogen bonds pull adjacent molecules closer, the interesting difference is the two solvent waters in the asymmetric unit, which form strong O—H···O hydrogen bonds with O atom of P═O,(Fig. 2). The waters take place of the adjacent bulky molecules to stabilize the crystal packing. As a result, the molecules pack in a different, much looser form in the crystal. And the calculated density of the crystal also confirms this point, 1.240 and 1.419 g cm^-3 for the title compoud and the previous structure, respectively.

The whole structure exhibits as a dimer of triarylphosphorus oxide through C1—C7 covalent bond. The bond lengths [1.803 (2)–1.812 (2) Å] and angles[104.05 (10)–107.27 (11)°] of C_aryl—P do not show large deviations from those observed in related structures (Meijboom, 2011; Wang, et al., 2011; Warsink, et al., 2011). Two methoxyphenyl rings locate almost perpendicular to each other, with a dihedral angle of 84.11(0.07)°.

Related literature top

For the synthesis of the title compound and its unsolvated crystal structure, see: Doherty et al. (2009). For similar structures, see: Meijboom (2011); Wang et al. (2011); Warsink et al. (2011).

Experimental top

The title compound was prepared according to the procedure of Doherty et al., (2009) through double cycloaddition-elimination by using 1,4-bis-(diphenylphosphinoyl)buta-1,3-diyne and 1-methoxy-1,3-cycolhexadiene, heated with microwave in toluene solution. Colourless blocks were obtained from acetone/water(1:1) solution after about a week at room temperature.

Computing details top

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

Figures top

	Fig. 1. View of the molecule of (I) showing displacement ellipsoids drawn at the 30% probability level. Hydrogen atoms were omitted for clarity.
	Fig. 2. The packing of the title compound, viewed down the a axis. Dashed lines indicate the O—H···O hydrogen bonds.

(6,6'-Dimethoxybiphenyl-2,2'-diyl)bis(diphenylphosphane) P,P'-dioxide dihydrate top

Crystal data top

C₃₈H₃₂O₄P₂·2H₂O	F(000) = 2736
M_r = 650.61	D_x = 1.240 Mg m⁻³
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4670 reflections
a = 13.108 (3) Å	θ = 2.6–67.7°
b = 15.650 (3) Å	µ = 1.50 mm⁻¹
c = 33.967 (7) Å	T = 296 K
V = 6968 (3) Å³	Block, colourless
Z = 8	0.23 × 0.10 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	6197 independent reflections
Radiation source: fine-focus sealed tube	4670 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 67.7°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→12
T_min = 0.725, T_max = 0.865	k = −18→18
31453 measured reflections	l = −35→40

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.066P)² + 1.3879P] where P = (F_o² + 2F_c²)/3
6197 reflections	(Δ/σ)_max = 0.001
415 parameters	Δρ_max = 0.20 e Å⁻³
3 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₃₈H₃₂O₄P₂·2H₂O	V = 6968 (3) Å³
M_r = 650.61	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 13.108 (3) Å	µ = 1.50 mm⁻¹
b = 15.650 (3) Å	T = 296 K
c = 33.967 (7) Å	0.23 × 0.10 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	6197 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4670 reflections with I > 2σ(I)
T_min = 0.725, T_max = 0.865	R_int = 0.042
31453 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	3 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
6197 reflections	Δρ_min = −0.29 e Å⁻³
415 parameters

Special details top

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
P1	0.80685 (4)	0.18583 (3)	0.593688 (18)	0.05612 (16)
P2	1.07260 (4)	0.30232 (4)	0.651596 (17)	0.05821 (17)
O1	1.10418 (14)	0.07362 (13)	0.67804 (5)	0.0805 (5)
O2	1.00948 (16)	0.01615 (12)	0.58155 (6)	0.0875 (6)
O3	0.87621 (12)	0.24506 (10)	0.57242 (5)	0.0680 (4)
O4	0.96975 (12)	0.30072 (10)	0.66970 (5)	0.0710 (4)
C1	0.96504 (16)	0.12224 (12)	0.64144 (6)	0.0516 (5)
C2	0.86030 (16)	0.13410 (12)	0.63672 (6)	0.0539 (5)
C3	0.79402 (19)	0.10720 (15)	0.66641 (7)	0.0682 (6)
H3A	0.7241	0.1153	0.6635	0.082*
C4	0.8310 (2)	0.06900 (16)	0.69975 (8)	0.0751 (7)
H4A	0.7858	0.0507	0.7191	0.090*
C5	0.9343 (2)	0.05729 (16)	0.70501 (7)	0.0699 (6)
H5A	0.9589	0.0320	0.7279	0.084*
C6	1.00078 (18)	0.08347 (14)	0.67601 (6)	0.0597 (5)
C7	1.04118 (15)	0.14815 (13)	0.61094 (6)	0.0515 (5)
C8	1.09387 (15)	0.22572 (14)	0.61251 (6)	0.0532 (5)
C9	1.16457 (18)	0.24536 (15)	0.58293 (7)	0.0641 (6)
H9A	1.2000	0.2968	0.5838	0.077*
C10	1.1816 (2)	0.18884 (17)	0.55269 (7)	0.0727 (7)
H10A	1.2285	0.2025	0.5331	0.087*
C11	1.1304 (2)	0.11233 (18)	0.55099 (7)	0.0728 (7)
H11A	1.1422	0.0747	0.5303	0.087*
C12	1.06147 (18)	0.09148 (15)	0.58007 (7)	0.0622 (6)
C13	1.0309 (4)	−0.0473 (2)	0.55322 (12)	0.1502 (19)
H13A	0.9883	−0.0962	0.5579	0.225*
H13B	1.1013	−0.0637	0.5552	0.225*
H13C	1.0176	−0.0251	0.5274	0.225*
C14	1.1479 (3)	0.0481 (2)	0.71429 (9)	0.1078 (11)
H14A	1.2206	0.0438	0.7114	0.162*
H14B	1.1207	−0.0065	0.7219	0.162*
H14C	1.1321	0.0896	0.7342	0.162*
C15	0.69724 (17)	0.24298 (13)	0.61195 (7)	0.0627 (6)
C16	0.5982 (2)	0.2192 (2)	0.60574 (14)	0.1231 (14)
H16A	0.5844	0.1698	0.5915	0.148*
C17	0.5185 (3)	0.2673 (3)	0.62022 (16)	0.152 (2)
H17A	0.4517	0.2492	0.6163	0.183*
C18	0.5367 (3)	0.3408 (2)	0.64014 (11)	0.1039 (10)
H18A	0.4828	0.3735	0.6497	0.125*
C19	0.6331 (3)	0.36566 (17)	0.64588 (9)	0.0855 (8)
H19A	0.6459	0.4163	0.6593	0.103*
C20	0.7139 (2)	0.31772 (15)	0.63230 (8)	0.0727 (6)
H20A	0.7804	0.3360	0.6369	0.087*
C21	0.75769 (17)	0.10246 (13)	0.56231 (6)	0.0573 (5)
C22	0.7201 (2)	0.12554 (17)	0.52578 (8)	0.0844 (8)
H22A	0.7222	0.1825	0.5181	0.101*
C23	0.6794 (3)	0.0651 (2)	0.50058 (8)	0.0949 (9)
H23A	0.6537	0.0815	0.4762	0.114*
C24	0.6771 (2)	−0.01876 (18)	0.51153 (8)	0.0778 (7)
H24A	0.6497	−0.0594	0.4946	0.093*
C25	0.7145 (2)	−0.04304 (15)	0.54702 (8)	0.0721 (7)
H25A	0.7129	−0.1003	0.5543	0.087*
C26	0.7550 (2)	0.01716 (14)	0.57237 (7)	0.0670 (6)
H26A	0.7809	−0.0002	0.5966	0.080*
C27	1.09683 (17)	0.40435 (14)	0.62868 (7)	0.0587 (5)
C28	1.02525 (18)	0.43283 (15)	0.60170 (7)	0.0668 (6)
H28A	0.9701	0.3982	0.5951	0.080*
C29	1.0353 (2)	0.51243 (16)	0.58446 (8)	0.0740 (7)
H29A	0.9868	0.5313	0.5664	0.089*
C30	1.1163 (2)	0.56346 (16)	0.59384 (8)	0.0738 (7)
H30A	1.1224	0.6172	0.5824	0.089*
C31	1.1881 (2)	0.53592 (16)	0.61996 (9)	0.0782 (7)
H31A	1.2435	0.5707	0.6259	0.094*
C32	1.17926 (19)	0.45643 (16)	0.63770 (8)	0.0726 (7)
H32A	1.2284	0.4381	0.6556	0.087*
C33	1.1719 (2)	0.28665 (16)	0.68767 (7)	0.0703 (6)
C34	1.1509 (3)	0.3085 (3)	0.72569 (10)	0.1249 (13)
H34A	1.0867	0.3293	0.7323	0.150*
C35	1.2251 (5)	0.2998 (4)	0.75440 (12)	0.168 (2)
H35A	1.2104	0.3166	0.7800	0.202*
C36	1.3176 (4)	0.2678 (3)	0.74624 (13)	0.1293 (16)
H36A	1.3661	0.2615	0.7660	0.155*
C37	1.3394 (3)	0.2448 (3)	0.70872 (12)	0.1192 (13)
H37A	1.4035	0.2230	0.7026	0.143*
C38	1.2661 (3)	0.2537 (2)	0.67941 (9)	0.0958 (9)
H38A	1.2814	0.2370	0.6538	0.115*
O2'	0.9356 (2)	0.2718 (2)	0.49425 (8)	0.1491 (11)
H2'A	0.9192	0.2565	0.5174	0.224*
H2'B	0.9978	0.2869	0.4960	0.224*
O1'	0.9143 (4)	0.4666 (3)	0.69732 (12)	0.228 (2)
H1'A	0.9114	0.4391	0.6758	0.342*
H1'B	0.9306	0.4285	0.7140	0.342*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0547 (3)	0.0467 (3)	0.0669 (4)	−0.0015 (2)	0.0027 (2)	0.0036 (2)
P2	0.0619 (3)	0.0572 (3)	0.0556 (3)	−0.0052 (2)	0.0050 (2)	−0.0018 (3)
O1	0.0752 (11)	0.1074 (14)	0.0588 (10)	0.0052 (10)	−0.0087 (8)	0.0174 (9)
O2	0.1042 (15)	0.0723 (11)	0.0862 (13)	−0.0095 (10)	0.0138 (10)	−0.0268 (10)
O3	0.0634 (9)	0.0622 (9)	0.0785 (11)	−0.0065 (7)	0.0018 (8)	0.0160 (8)
O4	0.0722 (10)	0.0677 (10)	0.0731 (10)	−0.0086 (8)	0.0224 (8)	−0.0119 (8)
C1	0.0609 (12)	0.0465 (10)	0.0474 (11)	−0.0029 (9)	0.0048 (9)	−0.0025 (9)
C2	0.0591 (12)	0.0454 (10)	0.0571 (12)	−0.0022 (9)	0.0062 (9)	−0.0018 (9)
C3	0.0646 (14)	0.0648 (14)	0.0753 (16)	−0.0039 (11)	0.0159 (11)	0.0025 (12)
C4	0.0916 (19)	0.0719 (15)	0.0618 (15)	−0.0090 (13)	0.0237 (13)	0.0038 (12)
C5	0.0956 (19)	0.0663 (14)	0.0479 (13)	−0.0063 (13)	0.0060 (12)	0.0021 (11)
C6	0.0712 (14)	0.0584 (13)	0.0497 (12)	−0.0036 (10)	0.0000 (10)	−0.0021 (10)
C7	0.0524 (11)	0.0572 (11)	0.0448 (11)	0.0051 (9)	−0.0008 (8)	0.0027 (9)
C8	0.0519 (12)	0.0597 (12)	0.0482 (11)	0.0046 (9)	0.0035 (8)	0.0033 (9)
C9	0.0623 (13)	0.0659 (13)	0.0642 (14)	0.0042 (11)	0.0123 (10)	0.0116 (11)
C10	0.0767 (16)	0.0872 (18)	0.0543 (14)	0.0201 (14)	0.0200 (11)	0.0167 (12)
C11	0.0863 (18)	0.0801 (17)	0.0522 (13)	0.0184 (14)	0.0109 (11)	−0.0026 (12)
C12	0.0686 (14)	0.0652 (13)	0.0528 (12)	0.0090 (11)	0.0026 (10)	−0.0033 (10)
C13	0.245 (6)	0.096 (3)	0.110 (3)	−0.033 (3)	0.049 (3)	−0.046 (2)
C14	0.105 (2)	0.150 (3)	0.0676 (18)	0.018 (2)	−0.0213 (16)	0.0263 (19)
C15	0.0613 (13)	0.0479 (11)	0.0788 (15)	−0.0004 (10)	0.0012 (11)	−0.0032 (11)
C16	0.0627 (18)	0.093 (2)	0.213 (4)	−0.0049 (15)	0.009 (2)	−0.073 (3)
C17	0.065 (2)	0.135 (3)	0.257 (6)	0.007 (2)	0.014 (3)	−0.096 (4)
C18	0.089 (2)	0.088 (2)	0.134 (3)	0.0257 (18)	0.0201 (19)	−0.020 (2)
C19	0.112 (2)	0.0569 (14)	0.088 (2)	0.0085 (15)	0.0185 (16)	−0.0100 (13)
C20	0.0800 (17)	0.0644 (14)	0.0738 (16)	−0.0074 (12)	0.0047 (12)	−0.0072 (12)
C21	0.0608 (13)	0.0540 (12)	0.0570 (12)	0.0011 (9)	0.0060 (10)	0.0006 (10)
C22	0.120 (2)	0.0645 (15)	0.0687 (16)	−0.0097 (15)	−0.0074 (15)	0.0094 (13)
C23	0.137 (3)	0.091 (2)	0.0572 (15)	−0.0121 (19)	−0.0136 (16)	0.0031 (15)
C24	0.0936 (19)	0.0745 (17)	0.0652 (16)	−0.0039 (14)	0.0093 (13)	−0.0166 (13)
C25	0.0838 (17)	0.0520 (13)	0.0804 (17)	0.0009 (11)	0.0039 (13)	−0.0065 (12)
C26	0.0778 (16)	0.0547 (12)	0.0686 (15)	0.0027 (11)	−0.0018 (12)	0.0009 (11)
C27	0.0562 (12)	0.0574 (12)	0.0626 (13)	−0.0039 (9)	0.0022 (10)	−0.0029 (10)
C28	0.0606 (14)	0.0619 (13)	0.0779 (16)	−0.0073 (11)	−0.0072 (11)	0.0004 (12)
C29	0.0722 (16)	0.0658 (15)	0.0841 (18)	0.0024 (12)	−0.0062 (12)	0.0043 (13)
C30	0.0782 (17)	0.0580 (13)	0.0851 (18)	−0.0042 (12)	0.0047 (13)	0.0057 (13)
C31	0.0718 (16)	0.0683 (15)	0.094 (2)	−0.0198 (12)	−0.0023 (14)	0.0010 (14)
C32	0.0649 (15)	0.0703 (15)	0.0827 (17)	−0.0114 (11)	−0.0117 (12)	0.0052 (13)
C33	0.0855 (18)	0.0676 (14)	0.0579 (14)	−0.0066 (12)	−0.0076 (12)	0.0045 (11)
C34	0.139 (3)	0.172 (4)	0.0640 (19)	0.026 (3)	−0.0141 (19)	−0.015 (2)
C35	0.192 (5)	0.242 (6)	0.071 (2)	0.030 (5)	−0.041 (3)	−0.024 (3)
C36	0.163 (4)	0.127 (3)	0.098 (3)	−0.025 (3)	−0.065 (3)	0.027 (2)
C37	0.103 (3)	0.139 (3)	0.116 (3)	0.000 (2)	−0.041 (2)	0.022 (3)
C38	0.091 (2)	0.120 (2)	0.0771 (18)	0.0091 (18)	−0.0196 (15)	0.0020 (17)
O2'	0.147 (2)	0.198 (3)	0.1023 (18)	0.006 (2)	0.0169 (16)	0.027 (2)
O1'	0.287 (5)	0.217 (4)	0.179 (3)	0.099 (4)	0.046 (3)	−0.055 (3)

Geometric parameters (Å, º) top

P1—O3	1.4859 (16)	C18—C19	1.337 (4)
P1—C15	1.802 (2)	C18—H18A	0.9300
P1—C21	1.804 (2)	C19—C20	1.377 (4)
P1—C2	1.812 (2)	C19—H19A	0.9300
P2—O4	1.4819 (16)	C20—H20A	0.9300
P2—C33	1.804 (3)	C21—C26	1.378 (3)
P2—C27	1.804 (2)	C21—C22	1.383 (3)
P2—C8	1.810 (2)	C22—C23	1.383 (4)
O1—C6	1.366 (3)	C22—H22A	0.9300
O1—C14	1.416 (3)	C23—C24	1.364 (4)
O2—C12	1.363 (3)	C23—H23A	0.9300
O2—C13	1.411 (4)	C24—C25	1.356 (4)
C1—C2	1.395 (3)	C24—H24A	0.9300
C1—C6	1.402 (3)	C25—C26	1.383 (3)
C1—C7	1.495 (3)	C25—H25A	0.9300
C2—C3	1.396 (3)	C26—H26A	0.9300
C3—C4	1.369 (4)	C27—C28	1.385 (3)
C3—H3A	0.9300	C27—C32	1.388 (3)
C4—C5	1.379 (4)	C28—C29	1.383 (3)
C4—H4A	0.9300	C28—H28A	0.9300
C5—C6	1.377 (3)	C29—C30	1.366 (4)
C5—H5A	0.9300	C29—H29A	0.9300
C7—C8	1.398 (3)	C30—C31	1.364 (4)
C7—C12	1.399 (3)	C30—H30A	0.9300
C8—C9	1.401 (3)	C31—C32	1.387 (3)
C9—C10	1.374 (3)	C31—H31A	0.9300
C9—H9A	0.9300	C32—H32A	0.9300
C10—C11	1.374 (4)	C33—C34	1.364 (4)
C10—H10A	0.9300	C33—C38	1.368 (4)
C11—C12	1.378 (3)	C34—C35	1.384 (6)
C11—H11A	0.9300	C34—H34A	0.9300
C13—H13A	0.9600	C35—C36	1.341 (6)
C13—H13B	0.9600	C35—H35A	0.9300
C13—H13C	0.9600	C36—C37	1.355 (6)
C14—H14A	0.9600	C36—H36A	0.9300
C14—H14B	0.9600	C37—C38	1.391 (4)
C14—H14C	0.9600	C37—H37A	0.9300
C15—C16	1.367 (4)	C38—H38A	0.9300
C15—C20	1.376 (3)	O2'—H2'A	0.8497
C16—C17	1.378 (4)	O2'—H2'B	0.8501
C16—H16A	0.9300	O1'—H1'A	0.8498
C17—C18	1.356 (5)	O1'—H1'B	0.8500
C17—H17A	0.9300

O3—P1—C15	110.21 (10)	C18—C17—C16	120.6 (3)
O3—P1—C21	112.49 (10)	C18—C17—H17A	119.7
C15—P1—C21	106.11 (11)	C16—C17—H17A	119.7
O3—P1—C2	115.74 (10)	C19—C18—C17	119.0 (3)
C15—P1—C2	104.62 (11)	C19—C18—H18A	120.5
C21—P1—C2	106.96 (10)	C17—C18—H18A	120.5
O4—P2—C33	111.83 (12)	C18—C19—C20	121.3 (3)
O4—P2—C27	110.74 (10)	C18—C19—H19A	119.3
C33—P2—C27	106.64 (11)	C20—C19—H19A	119.3
O4—P2—C8	115.67 (10)	C15—C20—C19	120.6 (3)
C33—P2—C8	107.27 (11)	C15—C20—H20A	119.7
C27—P2—C8	104.04 (10)	C19—C20—H20A	119.7
C6—O1—C14	118.5 (2)	C26—C21—C22	117.8 (2)
C12—O2—C13	119.0 (2)	C26—C21—P1	124.26 (18)
C2—C1—C6	118.86 (19)	C22—C21—P1	117.94 (18)
C2—C1—C7	122.79 (18)	C23—C22—C21	120.9 (2)
C6—C1—C7	118.35 (19)	C23—C22—H22A	119.5
C1—C2—C3	119.3 (2)	C21—C22—H22A	119.5
C1—C2—P1	122.21 (15)	C24—C23—C22	119.9 (3)
C3—C2—P1	118.48 (18)	C24—C23—H23A	120.1
C4—C3—C2	120.6 (2)	C22—C23—H23A	120.1
C4—C3—H3A	119.7	C25—C24—C23	120.2 (3)
C2—C3—H3A	119.7	C25—C24—H24A	119.9
C3—C4—C5	120.8 (2)	C23—C24—H24A	119.9
C3—C4—H4A	119.6	C24—C25—C26	120.1 (2)
C5—C4—H4A	119.6	C24—C25—H25A	119.9
C6—C5—C4	119.3 (2)	C26—C25—H25A	119.9
C6—C5—H5A	120.4	C21—C26—C25	121.0 (2)
C4—C5—H5A	120.4	C21—C26—H26A	119.5
O1—C6—C5	123.9 (2)	C25—C26—H26A	119.5
O1—C6—C1	114.99 (19)	C28—C27—C32	119.0 (2)
C5—C6—C1	121.1 (2)	C28—C27—P2	116.79 (17)
C8—C7—C12	119.0 (2)	C32—C27—P2	124.16 (19)
C8—C7—C1	122.63 (18)	C29—C28—C27	120.4 (2)
C12—C7—C1	118.33 (19)	C29—C28—H28A	119.8
C7—C8—C9	119.4 (2)	C27—C28—H28A	119.8
C7—C8—P2	121.80 (15)	C30—C29—C28	120.1 (2)
C9—C8—P2	118.85 (18)	C30—C29—H29A	119.9
C10—C9—C8	120.2 (2)	C28—C29—H29A	119.9
C10—C9—H9A	119.9	C31—C30—C29	120.2 (2)
C8—C9—H9A	119.9	C31—C30—H30A	119.9
C9—C10—C11	120.9 (2)	C29—C30—H30A	119.9
C9—C10—H10A	119.6	C30—C31—C32	120.6 (2)
C11—C10—H10A	119.6	C30—C31—H31A	119.7
C10—C11—C12	119.8 (2)	C32—C31—H31A	119.7
C10—C11—H11A	120.1	C31—C32—C27	119.7 (2)
C12—C11—H11A	120.1	C31—C32—H32A	120.1
O2—C12—C11	124.0 (2)	C27—C32—H32A	120.1
O2—C12—C7	115.2 (2)	C34—C33—C38	118.1 (3)
C11—C12—C7	120.8 (2)	C34—C33—P2	117.6 (3)
O2—C13—H13A	109.5	C38—C33—P2	124.3 (2)
O2—C13—H13B	109.5	C33—C34—C35	120.1 (4)
H13A—C13—H13B	109.5	C33—C34—H34A	120.0
O2—C13—H13C	109.5	C35—C34—H34A	120.0
H13A—C13—H13C	109.5	C36—C35—C34	121.8 (4)
H13B—C13—H13C	109.5	C36—C35—H35A	119.1
O1—C14—H14A	109.5	C34—C35—H35A	119.1
O1—C14—H14B	109.5	C35—C36—C37	119.0 (4)
H14A—C14—H14B	109.5	C35—C36—H36A	120.5
O1—C14—H14C	109.5	C37—C36—H36A	120.5
H14A—C14—H14C	109.5	C36—C37—C38	120.1 (4)
H14B—C14—H14C	109.5	C36—C37—H37A	120.0
C16—C15—C20	117.4 (2)	C38—C37—H37A	120.0
C16—C15—P1	124.7 (2)	C33—C38—C37	121.0 (3)
C20—C15—P1	117.90 (19)	C33—C38—H38A	119.5
C15—C16—C17	121.1 (3)	C37—C38—H38A	119.5
C15—C16—H16A	119.5	H2'A—O2'—H2'B	104.8
C17—C16—H16A	119.5	H1'A—O1'—H1'B	103.5

C6—C1—C2—C3	0.0 (3)	C21—P1—C15—C20	−170.98 (19)
C7—C1—C2—C3	179.25 (19)	C2—P1—C15—C20	76.1 (2)
C6—C1—C2—P1	178.48 (16)	C20—C15—C16—C17	−1.6 (6)
C7—C1—C2—P1	−2.3 (3)	P1—C15—C16—C17	−178.9 (4)
O3—P1—C2—C1	−24.2 (2)	C15—C16—C17—C18	1.8 (8)
C15—P1—C2—C1	−145.72 (17)	C16—C17—C18—C19	−0.6 (7)
C21—P1—C2—C1	101.98 (18)	C17—C18—C19—C20	−0.6 (6)
O3—P1—C2—C3	154.22 (17)	C16—C15—C20—C19	0.4 (4)
C15—P1—C2—C3	32.7 (2)	P1—C15—C20—C19	177.9 (2)
C21—P1—C2—C3	−79.55 (19)	C18—C19—C20—C15	0.7 (5)
C1—C2—C3—C4	−0.5 (3)	O3—P1—C21—C26	133.4 (2)
P1—C2—C3—C4	−178.99 (19)	C15—P1—C21—C26	−106.0 (2)
C2—C3—C4—C5	0.9 (4)	C2—P1—C21—C26	5.3 (2)
C3—C4—C5—C6	−0.9 (4)	O3—P1—C21—C22	−46.7 (2)
C14—O1—C6—C5	−10.7 (4)	C15—P1—C21—C22	73.9 (2)
C14—O1—C6—C1	169.9 (2)	C2—P1—C21—C22	−174.8 (2)
C4—C5—C6—O1	−178.9 (2)	C26—C21—C22—C23	1.2 (4)
C4—C5—C6—C1	0.4 (4)	P1—C21—C22—C23	−178.7 (3)
C2—C1—C6—O1	179.40 (19)	C21—C22—C23—C24	−0.7 (5)
C7—C1—C6—O1	0.1 (3)	C22—C23—C24—C25	0.0 (5)
C2—C1—C6—C5	0.0 (3)	C23—C24—C25—C26	0.2 (4)
C7—C1—C6—C5	−179.3 (2)	C22—C21—C26—C25	−1.1 (4)
C2—C1—C7—C8	96.8 (3)	P1—C21—C26—C25	178.8 (2)
C6—C1—C7—C8	−84.0 (3)	C24—C25—C26—C21	0.4 (4)
C2—C1—C7—C12	−84.4 (3)	O4—P2—C27—C28	−53.6 (2)
C6—C1—C7—C12	94.8 (2)	C33—P2—C27—C28	−175.45 (19)
C12—C7—C8—C9	0.9 (3)	C8—P2—C27—C28	71.3 (2)
C1—C7—C8—C9	179.64 (19)	O4—P2—C27—C32	123.6 (2)
C12—C7—C8—P2	−179.68 (16)	C33—P2—C27—C32	1.7 (2)
C1—C7—C8—P2	−0.9 (3)	C8—P2—C27—C32	−111.5 (2)
O4—P2—C8—C7	−27.9 (2)	C32—C27—C28—C29	−0.8 (4)
C33—P2—C8—C7	97.62 (19)	P2—C27—C28—C29	176.4 (2)
C27—P2—C8—C7	−149.62 (17)	C27—C28—C29—C30	0.3 (4)
O4—P2—C8—C9	151.54 (17)	C28—C29—C30—C31	0.6 (4)
C33—P2—C8—C9	−82.90 (19)	C29—C30—C31—C32	−0.9 (4)
C27—P2—C8—C9	29.9 (2)	C30—C31—C32—C27	0.2 (4)
C7—C8—C9—C10	0.1 (3)	C28—C27—C32—C31	0.6 (4)
P2—C8—C9—C10	−179.40 (18)	P2—C27—C32—C31	−176.5 (2)
C8—C9—C10—C11	−0.3 (4)	O4—P2—C33—C34	−25.2 (3)
C9—C10—C11—C12	−0.5 (4)	C27—P2—C33—C34	96.0 (3)
C13—O2—C12—C11	4.0 (4)	C8—P2—C33—C34	−153.0 (3)
C13—O2—C12—C7	−175.4 (3)	O4—P2—C33—C38	154.3 (2)
C10—C11—C12—O2	−177.9 (2)	C27—P2—C33—C38	−84.5 (3)
C10—C11—C12—C7	1.4 (4)	C8—P2—C33—C38	26.4 (3)
C8—C7—C12—O2	177.8 (2)	C38—C33—C34—C35	2.1 (6)
C1—C7—C12—O2	−1.1 (3)	P2—C33—C34—C35	−178.4 (4)
C8—C7—C12—C11	−1.6 (3)	C33—C34—C35—C36	−1.9 (8)
C1—C7—C12—C11	179.5 (2)	C34—C35—C36—C37	1.1 (8)
O3—P1—C15—C16	128.4 (3)	C35—C36—C37—C38	−0.6 (7)
C21—P1—C15—C16	6.4 (3)	C34—C33—C38—C37	−1.6 (5)
C2—P1—C15—C16	−106.5 (3)	P2—C33—C38—C37	178.9 (3)
O3—P1—C15—C20	−48.9 (2)	C36—C37—C38—C33	0.9 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1′—H1′A···O4	0.85	2.31	2.854 (4)	123
O2′—H2′A···O3	0.85	1.96	2.799 (3)	169

Experimental details

Crystal data
Chemical formula	C₃₈H₃₂O₄P₂·2H₂O
M_r	650.61
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	13.108 (3), 15.650 (3), 33.967 (7)
V (Å³)	6968 (3)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	1.50
Crystal size (mm)	0.23 × 0.10 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.725, 0.865
No. of measured, independent and observed [I > 2σ(I)] reflections	31453, 6197, 4670
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.130, 1.03
No. of reflections	6197
No. of parameters	415
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.29

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1'—H1'A···O4	0.85	2.31	2.854 (4)	123
O2'—H2'A···O3	0.85	1.96	2.799 (3)	169

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Doherty, S., Smyth, C. H., Harrington, R. W. & Clegg, W. (2009). Organometallics, 28, 5273–5276. Web of Science CSD CrossRef CAS Google Scholar
Meijboom, R. (2011). Acta Cryst. E67, m1663. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, H., Zhang, X.-M., Li, P. & Chen, H.-Y. (2011). Acta Cryst. E67, o3149. Web of Science CSD CrossRef IUCr Journals Google Scholar
Warsink, S., Koen, R. & Roodt, A. (2011). Acta Cryst. E67, m1666. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 3| March 2012| Page o804

doi:10.1107/S1600536812005314

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(6,6′-Dimeth­­oxy­bi­phenyl-2,2′-di­yl)bis­(di­phenyl­phosphane) P,P′-dioxide dihydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

(6,6′-Dimethoxybiphenyl-2,2′-diyl)bis(diphenylphosphane) P,P′-dioxide dihydrate