1,1-(Biphenyl-2,2′-diyldi­oxy)-3,3,5,5-tetra­kis­(4-bromo­methyl­phen­oxy)cyclo­triphosphazene

Han, R.; Chai, M.-M.; Yang, J.-L.; Ye, Y.

doi:10.1107/S1600536811016047

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1298

doi:10.1107/S1600536811016047

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1,1-(Biphenyl-2,2′-diyldioxy)-3,3,5,5-tetrakis(4-bromomethylphenoxy)cyclotriphosphazene

Rui Han,^a Mei-Mei Chai,^a Jun-Liang Yang ^a and Yong Ye ^a ^*

^aPhosphorus Chemical Engineering Research Center of Henan Province, Department of Chemistry, Zhengzhou University, Zhengzhou 450052, People's Republic of China
^*Correspondence e-mail: yeyong@zzu.edu.cn

(Received 6 April 2011; accepted 27 April 2011; online 7 May 2011)

In the title compound, C₄₀H₃₂Br₄N₃O₆P₃, the cyclotriphosphazene ring adopts a planar conformation, with an r.m.s. deviation of 0.0247 Å. In the crystal, there is a weak intermolecular C—H⋯O hydrogen bond as well as short intermolecular Br⋯Br contacts [3.3352 (12) Å].

Related literature

For general background to cyclotriphosphazenes, see: Manners (1996). For the applications of cyclotriphosphazene derivatives as flame retardants, see: Allcock (1977 ); as elastomers, see: Allcock (2000 ); as biomaterials, see: Trollsa & Hedrick (1998 ); as artificial nucleases, see: Wang, Ye, Zhong et al. (2009 ); Wang, Ye, Ju et al. (2009 ).

Experimental

Crystal data

C₄₀H₃₂Br₄N₃O₆P₃
M_r = 1063.24
Monoclinic, P 2₁ /n
a = 10.991 (2) Å
b = 28.417 (6) Å
c = 14.008 (3) Å
β = 105.47 (3)°
V = 4216.7 (15) Å³
Z = 4
Mo Kα radiation
μ = 3.98 mm⁻¹
T = 293 K
0.24 × 0.20 × 0.18 mm

Data collection

Bruker P4 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.392, T_max = 0.520
52073 measured reflections
9978 independent reflections
6049 reflections with I > 2σ(I)
R_int = 0.075

Refinement

R[F² > 2σ(F²)] = 0.077
wR(F²) = 0.192
S = 1.11
9978 reflections
505 parameters
H-atom parameters constrained
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C33—H33A⋯O1ⁱ	0.97	2.60	3.525 (8)	160
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: XSCANS (Bruker, 2008); cell refinement: XSCANS; 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 global, I. DOI: 10.1107/S1600536811016047/zs2109sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016047/zs2109Isup2.hkl

checkCIF report

Comment top

Cyclotriphosphazenes are of considerable interest not only because of their wide spectrum of chemical and physical properties, but also their importance in synthetic chemistry (Manners, 1996). Different side-group substituents affect the chemical and physical properties of the ring systems in high polymers based on a phosphazene skeleton. Various cyclotriphosphazenes have been successfully developed for a variety of applications, such as flame retardants (Allcock, 1977), elastomers (Allcock, 2000) and biomaterials (Trollsa & Hedrick, 1998), achieved by varying the nature of the substituent side group. Recently, some polydentate cyclotriphosphazene ligands were reported, which showed good nuclease activity with hydrolytic cleavage ability (Wang, Ye, Zhong et al., 2009; Wang, Ye, Ju et al., 2009). To obtain more insight into the selective recognization and efficient cleavage of DNA by different metal complexes of cyclotriphosphazene, the title compound, C₄₀H₃₂Br₄N₃O₆P₃ (I), was synthesized and its crystal structure is reported here.

In the crystal structure of (I) (Fig. 1), the part of cyclotriphosphazene ring adopts a planar conformation with an r.m.s. deviation of 0.0247 Å. There are short intermolecular Br···Br contacts: Br1···Br2ⁱⁱ [3.3352 (12) Å] and Br3···Br4ⁱⁱⁱ [3.5868 (15) Å] [for symmetry codes: (ii) -x - 1/2, y - 1/2, -z + 1/2; (iii) -x + 1/2, y - 1/2, -z + 1/2]. The crystal structure is stabilized by weak intermolecular C—H···O hydrogen bond (Table 1).

Related literature top

For general background to cyclotriphosphazenes, see: Manners (1996). For the applications of cyclotriphosphazene derivatives as flame retardants, see: Allcock (1977); as elastomers, see: Allcock (2000); as biomaterials, see: Trollsa & Hedrick (1998); as artificial nucleases, see: Wang, Ye, Zhong et al. (2009); Wang, Ye, Ju et al. (2009).

Experimental top

To 30 ml of THF 2,2'-biphenyldioxy-3,3,5,5-tetrakis(4-hydroxymethylphenoxy)- cyclotriphosphazene (1.622 g, 2 mmol) was added under argon. Then, 1.1 ml of phosphorus tribromide in 10 ml of THF was added dropwise and the mixture was stirred for 5 h. The organic solvent was removed under reduced pressure and the residue was dissolved in CHCl₃. The residue washed with aq. K₂CO₃ and extracted with CHCl₃, the organic layer was dried over Na₂SO₄ and then evaporated under reduced pressure. The remaining residue was purified by silica gel column chromatography (CH₂Cl₂/PE) to provide title compound which was recrystallized from CH₂Cl₂ and single crystals of (I) were obtained by slow evaporation.

Computing details top

Data collection: XSCANS (Bruker, 2008); cell refinement: XSCANS (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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. Molecular configuration and atom numbering scheme for (I), with displacement ellipsoids drawn at the 20% probability level.

1,1-(Biphenyl-2,2'-diyldioxy)-3,3,5,5-tetrakis(4- bromomethylphenoxy)cyclotriphosphazene top

Crystal data top

C₄₀H₃₂Br₄N₃O₆P₃	F(000) = 2104
M_r = 1063.24	D_x = 1.675 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7462 reflections
a = 10.991 (2) Å	θ = 2.1–27.9°
b = 28.417 (6) Å	µ = 3.98 mm⁻¹
c = 14.008 (3) Å	T = 293 K
β = 105.47 (3)°	Prism, colorless
V = 4216.7 (15) Å³	0.24 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker P4 CCD diffractometer	9978 independent reflections
Radiation source: fine-focus sealed tube	6049 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.075
ω scans	θ_max = 27.9°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→14
T_min = 0.392, T_max = 0.520	k = −37→37
52073 measured reflections	l = −18→18

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.192	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0761P)²] where P = (F_o² + 2F_c²)/3
9978 reflections	(Δ/σ)_max = 0.001
505 parameters	Δρ_max = 0.82 e Å⁻³
0 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

C₄₀H₃₂Br₄N₃O₆P₃	V = 4216.7 (15) Å³
M_r = 1063.24	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.991 (2) Å	µ = 3.98 mm⁻¹
b = 28.417 (6) Å	T = 293 K
c = 14.008 (3) Å	0.24 × 0.20 × 0.18 mm
β = 105.47 (3)°

Data collection top

Bruker P4 CCD diffractometer	9978 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	6049 reflections with I > 2σ(I)
T_min = 0.392, T_max = 0.520	R_int = 0.075
52073 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.192	H-atom parameters constrained
S = 1.11	Δρ_max = 0.82 e Å⁻³
9978 reflections	Δρ_min = −0.71 e Å⁻³
505 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
Br1	−0.08346 (6)	0.09289 (3)	0.36653 (6)	0.0732 (3)
Br2	−0.10180 (6)	0.59356 (3)	0.19304 (6)	0.0773 (3)
Br3	0.41308 (8)	0.13542 (3)	0.06958 (6)	0.0843 (3)
Br4	0.24692 (10)	0.53274 (3)	0.55072 (7)	0.0985 (3)
C1	−0.1461 (5)	0.3971 (2)	0.2173 (4)	0.0397 (12)
C2	−0.1438 (5)	0.4452 (2)	0.2072 (4)	0.0478 (14)
H2	−0.0683	0.4617	0.2283	0.057*
C3	−0.2555 (6)	0.4686 (2)	0.1653 (5)	0.0596 (17)
H3	−0.2547	0.5010	0.1558	0.072*
C4	−0.3689 (6)	0.4443 (2)	0.1372 (5)	0.0605 (17)
H4	−0.4442	0.4604	0.1114	0.073*
C5	−0.3695 (5)	0.3956 (2)	0.1477 (4)	0.0505 (15)
H5	−0.4457	0.3794	0.1284	0.061*
C6	−0.2570 (5)	0.37038 (19)	0.1869 (4)	0.0405 (13)
C7	−0.2574 (5)	0.3188 (2)	0.1952 (4)	0.0397 (12)
C8	−0.3569 (5)	0.2945 (2)	0.2200 (4)	0.0531 (15)
H8	−0.4232	0.3114	0.2329	0.064*
C9	−0.3574 (6)	0.2458 (2)	0.2256 (5)	0.0616 (17)
H9	−0.4243	0.2304	0.2410	0.074*
C10	−0.2592 (6)	0.2202 (2)	0.2083 (5)	0.0599 (17)
H10	−0.2593	0.1876	0.2134	0.072*
C11	−0.1597 (5)	0.2428 (2)	0.1833 (4)	0.0514 (15)
H11	−0.0936	0.2255	0.1713	0.062*
C12	−0.1602 (5)	0.2911 (2)	0.1766 (4)	0.0408 (13)
C13	0.2596 (5)	0.21640 (18)	0.3066 (4)	0.0394 (12)
C14	0.1915 (6)	0.1900 (2)	0.2275 (4)	0.0555 (16)
H14	0.1855	0.1997	0.1630	0.067*
C15	0.1329 (6)	0.1493 (2)	0.2442 (5)	0.0600 (17)
H15	0.0845	0.1322	0.1910	0.072*
C16	0.1454 (5)	0.13370 (19)	0.3407 (5)	0.0506 (15)
C17	0.2122 (6)	0.1612 (2)	0.4168 (5)	0.0582 (16)
H17	0.2182	0.1518	0.4815	0.070*
C18	0.2703 (6)	0.2019 (2)	0.4018 (4)	0.0551 (16)
H18	0.3163	0.2195	0.4552	0.066*
C19	0.0912 (6)	0.0870 (2)	0.3589 (6)	0.069 (2)
H19A	0.1424	0.0739	0.4204	0.082*
H19B	0.0942	0.0655	0.3058	0.082*
C20	0.2409 (5)	0.46520 (19)	0.1584 (4)	0.0443 (14)
C21	0.2325 (6)	0.4852 (2)	0.2471 (5)	0.0619 (17)
H21	0.2668	0.4699	0.3069	0.074*
C22	0.1733 (6)	0.5276 (2)	0.2451 (5)	0.0606 (17)
H22	0.1700	0.5415	0.3044	0.073*
C23	0.1184 (5)	0.5500 (2)	0.1571 (6)	0.0575 (17)
C24	0.1274 (5)	0.5302 (2)	0.0719 (5)	0.0545 (16)
H24	0.0915	0.5455	0.0123	0.065*
C25	0.1886 (5)	0.4877 (2)	0.0705 (4)	0.0505 (15)
H25	0.1943	0.4747	0.0109	0.061*
C26	0.0582 (6)	0.5975 (2)	0.1576 (7)	0.086 (3)
H26A	0.0436	0.6116	0.0924	0.104*
H26B	0.1156	0.6178	0.2045	0.104*
C27	0.2824 (5)	0.3118 (2)	0.0172 (4)	0.0453 (13)
C28	0.1792 (6)	0.2826 (2)	0.0044 (4)	0.0545 (15)
H28	0.1028	0.2937	0.0120	0.065*
C29	0.1932 (6)	0.2355 (2)	−0.0206 (4)	0.0580 (16)
H29	0.1246	0.2153	−0.0299	0.070*
C30	0.3068 (6)	0.2184 (2)	−0.0318 (4)	0.0518 (15)
C31	0.4050 (6)	0.2488 (2)	−0.0236 (5)	0.0591 (16)
H31	0.4797	0.2380	−0.0351	0.071*
C32	0.3950 (5)	0.2958 (2)	0.0020 (4)	0.0538 (15)
H32	0.4630	0.3162	0.0088	0.065*
C33	0.3209 (7)	0.1675 (2)	−0.0525 (5)	0.0693 (19)
H33A	0.3666	0.1641	−0.1025	0.083*
H33B	0.2383	0.1533	−0.0775	0.083*
C34	0.3556 (5)	0.3579 (2)	0.4642 (4)	0.0453 (14)
C35	0.4494 (6)	0.3902 (2)	0.4700 (5)	0.0605 (17)
H35	0.5128	0.3846	0.4388	0.073*
C36	0.4494 (7)	0.4315 (2)	0.5229 (5)	0.0670 (18)
H36	0.5131	0.4536	0.5274	0.080*
C37	0.3557 (8)	0.4398 (3)	0.5684 (5)	0.073 (2)
C38	0.2603 (8)	0.4073 (3)	0.5598 (5)	0.081 (2)
H38	0.1958	0.4134	0.5896	0.097*
C39	0.2586 (6)	0.3658 (2)	0.5074 (5)	0.0678 (19)
H39	0.1939	0.3440	0.5017	0.081*
C40	0.3541 (10)	0.4844 (3)	0.6263 (6)	0.104 (3)
H40A	0.4395	0.4964	0.6490	0.125*
H40B	0.3253	0.4771	0.6843	0.125*
N1	0.1362 (4)	0.31181 (15)	0.2933 (3)	0.0398 (10)
N2	0.3402 (4)	0.34123 (15)	0.2342 (3)	0.0408 (10)
N3	0.1042 (4)	0.37315 (15)	0.1405 (3)	0.0410 (11)
O1	−0.0320 (3)	0.37457 (12)	0.2693 (3)	0.0400 (9)
O2	−0.0652 (3)	0.31282 (12)	0.1399 (2)	0.0386 (8)
O3	0.3244 (3)	0.25632 (12)	0.2862 (3)	0.0473 (9)
O4	0.3618 (3)	0.31523 (13)	0.4151 (3)	0.0467 (9)
O5	0.3091 (4)	0.42359 (13)	0.1597 (4)	0.0642 (12)
O6	0.2786 (4)	0.35924 (13)	0.0467 (3)	0.0504 (10)
P1	0.04465 (12)	0.34309 (5)	0.21146 (10)	0.0365 (3)
P2	0.28306 (12)	0.30824 (5)	0.30222 (11)	0.0394 (3)
P3	0.25256 (13)	0.37218 (5)	0.14930 (11)	0.0419 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0496 (4)	0.0666 (5)	0.1086 (6)	−0.0111 (3)	0.0299 (4)	−0.0175 (4)
Br2	0.0483 (4)	0.0767 (5)	0.1062 (6)	0.0045 (3)	0.0193 (4)	−0.0218 (4)
Br3	0.1166 (7)	0.0600 (5)	0.0737 (5)	0.0086 (4)	0.0206 (5)	0.0056 (4)
Br4	0.1407 (8)	0.0686 (5)	0.0916 (6)	0.0241 (5)	0.0405 (6)	0.0054 (4)
C1	0.037 (3)	0.048 (3)	0.038 (3)	0.001 (2)	0.015 (2)	−0.009 (2)
C2	0.047 (3)	0.043 (3)	0.060 (4)	−0.004 (3)	0.026 (3)	−0.008 (3)
C3	0.081 (5)	0.044 (4)	0.063 (4)	0.013 (3)	0.034 (4)	0.001 (3)
C4	0.051 (4)	0.063 (4)	0.068 (4)	0.020 (3)	0.016 (3)	−0.001 (3)
C5	0.045 (3)	0.052 (4)	0.055 (4)	0.005 (3)	0.014 (3)	−0.008 (3)
C6	0.039 (3)	0.046 (3)	0.038 (3)	0.005 (2)	0.011 (2)	0.004 (2)
C7	0.032 (3)	0.047 (3)	0.040 (3)	−0.003 (2)	0.011 (2)	0.001 (2)
C8	0.044 (3)	0.069 (4)	0.048 (4)	−0.008 (3)	0.015 (3)	−0.001 (3)
C9	0.060 (4)	0.065 (4)	0.064 (4)	−0.031 (4)	0.024 (3)	−0.002 (3)
C10	0.080 (5)	0.039 (3)	0.060 (4)	−0.018 (3)	0.018 (3)	−0.001 (3)
C11	0.051 (3)	0.039 (3)	0.061 (4)	−0.004 (3)	0.011 (3)	−0.005 (3)
C12	0.031 (3)	0.049 (3)	0.041 (3)	−0.004 (2)	0.007 (2)	0.000 (2)
C13	0.035 (3)	0.036 (3)	0.049 (3)	0.004 (2)	0.014 (2)	−0.002 (2)
C14	0.073 (4)	0.048 (4)	0.041 (4)	0.001 (3)	0.008 (3)	0.004 (3)
C15	0.063 (4)	0.052 (4)	0.056 (4)	−0.007 (3)	0.001 (3)	−0.012 (3)
C16	0.039 (3)	0.036 (3)	0.079 (5)	0.003 (3)	0.020 (3)	0.000 (3)
C17	0.075 (4)	0.057 (4)	0.045 (4)	−0.013 (3)	0.020 (3)	0.005 (3)
C18	0.066 (4)	0.056 (4)	0.039 (4)	−0.013 (3)	0.007 (3)	−0.001 (3)
C19	0.063 (4)	0.048 (4)	0.107 (6)	−0.003 (3)	0.045 (4)	0.001 (4)
C20	0.038 (3)	0.032 (3)	0.066 (4)	−0.001 (2)	0.020 (3)	0.004 (3)
C21	0.075 (4)	0.063 (4)	0.050 (4)	−0.001 (4)	0.019 (3)	0.011 (3)
C22	0.064 (4)	0.054 (4)	0.067 (4)	−0.001 (3)	0.023 (3)	−0.019 (3)
C23	0.044 (3)	0.043 (3)	0.089 (5)	−0.004 (3)	0.024 (3)	−0.008 (4)
C24	0.050 (4)	0.044 (3)	0.062 (4)	−0.007 (3)	0.001 (3)	0.013 (3)
C25	0.056 (4)	0.052 (4)	0.045 (4)	−0.008 (3)	0.016 (3)	−0.009 (3)
C26	0.061 (4)	0.047 (4)	0.161 (8)	0.000 (3)	0.046 (5)	0.000 (5)
C27	0.052 (3)	0.047 (3)	0.038 (3)	0.002 (3)	0.015 (3)	0.006 (2)
C28	0.051 (4)	0.064 (4)	0.052 (4)	−0.003 (3)	0.020 (3)	0.001 (3)
C29	0.059 (4)	0.066 (4)	0.049 (4)	−0.014 (3)	0.014 (3)	0.000 (3)
C30	0.062 (4)	0.049 (4)	0.041 (3)	−0.006 (3)	0.008 (3)	−0.005 (3)
C31	0.065 (4)	0.058 (4)	0.057 (4)	0.012 (3)	0.022 (3)	−0.006 (3)
C32	0.041 (3)	0.062 (4)	0.057 (4)	−0.001 (3)	0.013 (3)	0.003 (3)
C33	0.101 (5)	0.049 (4)	0.054 (4)	0.008 (4)	0.014 (4)	−0.006 (3)
C34	0.047 (3)	0.047 (3)	0.040 (3)	0.005 (3)	0.008 (3)	−0.005 (3)
C35	0.059 (4)	0.059 (4)	0.063 (4)	−0.004 (3)	0.015 (3)	−0.002 (3)
C36	0.076 (5)	0.051 (4)	0.070 (5)	−0.004 (4)	0.012 (4)	0.007 (3)
C37	0.099 (6)	0.056 (4)	0.059 (4)	0.006 (4)	0.012 (4)	−0.005 (3)
C38	0.103 (6)	0.088 (6)	0.065 (5)	0.017 (5)	0.046 (4)	−0.016 (4)
C39	0.069 (4)	0.068 (5)	0.076 (5)	−0.013 (4)	0.035 (4)	−0.012 (4)
C40	0.181 (9)	0.056 (5)	0.068 (5)	0.022 (5)	0.022 (5)	−0.005 (4)
N1	0.033 (2)	0.042 (3)	0.047 (3)	0.0026 (19)	0.016 (2)	0.004 (2)
N2	0.031 (2)	0.035 (2)	0.059 (3)	−0.0023 (19)	0.018 (2)	0.002 (2)
N3	0.034 (2)	0.037 (2)	0.053 (3)	0.0041 (19)	0.014 (2)	0.010 (2)
O1	0.0313 (19)	0.043 (2)	0.047 (2)	0.0017 (16)	0.0130 (16)	−0.0061 (17)
O2	0.0345 (18)	0.043 (2)	0.042 (2)	−0.0042 (16)	0.0176 (16)	−0.0089 (16)
O3	0.048 (2)	0.032 (2)	0.067 (3)	0.0024 (17)	0.0243 (19)	−0.0022 (18)
O4	0.041 (2)	0.043 (2)	0.052 (2)	0.0017 (17)	0.0053 (18)	−0.0025 (18)
O5	0.045 (2)	0.032 (2)	0.125 (4)	0.0020 (18)	0.040 (2)	0.004 (2)
O6	0.062 (2)	0.044 (2)	0.057 (2)	0.0070 (19)	0.036 (2)	0.0122 (19)
P1	0.0320 (7)	0.0372 (7)	0.0431 (8)	−0.0004 (6)	0.0148 (6)	−0.0016 (6)
P2	0.0346 (7)	0.0346 (7)	0.0494 (9)	0.0015 (6)	0.0117 (6)	−0.0005 (6)
P3	0.0394 (8)	0.0330 (7)	0.0592 (10)	0.0005 (6)	0.0236 (7)	0.0036 (6)

Geometric parameters (Å, º) top

Br1—C19	1.958 (6)	C23—C24	1.347 (9)
Br2—C26	1.953 (7)	C23—C26	1.503 (8)
Br3—C33	1.963 (6)	C24—C25	1.385 (8)
Br4—C40	1.932 (8)	C24—H24	0.9300
C1—C2	1.374 (7)	C25—H25	0.9300
C1—C6	1.403 (7)	C26—H26A	0.9700
C1—O1	1.423 (6)	C26—H26B	0.9700
C2—C3	1.382 (8)	C27—C28	1.379 (8)
C2—H2	0.9300	C27—C32	1.387 (8)
C3—C4	1.388 (9)	C27—O6	1.413 (7)
C3—H3	0.9300	C28—C29	1.401 (9)
C4—C5	1.392 (8)	C28—H28	0.9300
C4—H4	0.9300	C29—C30	1.387 (8)
C5—C6	1.407 (7)	C29—H29	0.9300
C5—H5	0.9300	C30—C31	1.363 (8)
C6—C7	1.470 (7)	C30—C33	1.492 (8)
C7—C12	1.407 (7)	C31—C32	1.397 (8)
C7—C8	1.414 (7)	C31—H31	0.9300
C8—C9	1.385 (8)	C32—H32	0.9300
C8—H8	0.9300	C33—H33A	0.9700
C9—C10	1.375 (9)	C33—H33B	0.9700
C9—H9	0.9300	C34—C35	1.367 (8)
C10—C11	1.391 (8)	C34—C39	1.378 (8)
C10—H10	0.9300	C34—O4	1.405 (6)
C11—C12	1.374 (7)	C35—C36	1.389 (9)
C11—H11	0.9300	C35—H35	0.9300
C12—O2	1.422 (6)	C36—C37	1.368 (10)
C13—C18	1.370 (8)	C36—H36	0.9300
C13—C14	1.382 (7)	C37—C38	1.377 (10)
C13—O3	1.409 (6)	C37—C40	1.507 (10)
C14—C15	1.373 (8)	C38—C39	1.386 (9)
C14—H14	0.9300	C38—H38	0.9300
C15—C16	1.393 (9)	C39—H39	0.9300
C15—H15	0.9300	C40—H40A	0.9700
C16—C17	1.368 (8)	C40—H40B	0.9700
C16—C19	1.503 (8)	N1—P1	1.581 (4)
C17—C18	1.364 (8)	N1—P2	1.589 (4)
C17—H17	0.9300	N2—P2	1.581 (4)
C18—H18	0.9300	N2—P3	1.583 (4)
C19—H19A	0.9700	N3—P1	1.579 (4)
C19—H19B	0.9700	N3—P3	1.602 (4)
C20—C25	1.371 (8)	O1—P1	1.591 (4)
C20—C21	1.390 (8)	O2—P1	1.599 (4)
C20—O5	1.398 (6)	O3—P2	1.577 (4)
C21—C22	1.366 (9)	O4—P2	1.600 (4)
C21—H21	0.9300	O5—P3	1.579 (4)
C22—C23	1.377 (9)	O6—P3	1.582 (4)
C22—H22	0.9300

C2—C1—C6	123.1 (5)	Br2—C26—H26A	109.5
C2—C1—O1	117.6 (5)	C23—C26—H26B	109.5
C6—C1—O1	119.1 (5)	Br2—C26—H26B	109.5
C1—C2—C3	118.9 (5)	H26A—C26—H26B	108.5
C1—C2—H2	120.0	C28—C27—C32	121.3 (6)
C3—C2—H2	120.0	C28—C27—O6	121.7 (5)
C2—C3—C4	120.6 (6)	C32—C27—O6	117.0 (5)
C4—C3—H3	120.0	C27—C28—C29	117.8 (6)
C2—C3—H3	120.0	C27—C28—H28	120.0
C3—C4—C5	119.7 (6)	C29—C28—H28	120.0
C3—C4—H4	120.0	C30—C29—C28	121.7 (6)
C5—C4—H4	120.0	C30—C29—H29	120.0
C4—C5—C6	121.2 (5)	C28—C29—H29	120.0
C4—C5—H5	120.0	C31—C30—C29	119.0 (6)
C6—C5—H5	120.0	C31—C30—C33	120.6 (6)
C1—C6—C5	116.4 (5)	C29—C30—C33	120.4 (6)
C1—C6—C7	122.5 (4)	C30—C31—C32	120.8 (6)
C5—C6—C7	121.1 (5)	C30—C31—H31	120.0
C12—C7—C8	116.5 (5)	C32—C31—H31	120.0
C12—C7—C6	121.7 (5)	C27—C32—C31	119.2 (6)
C8—C7—C6	121.8 (5)	C27—C32—H32	120.0
C9—C8—C7	121.1 (6)	C31—C32—H32	120.0
C9—C8—H8	120.0	C30—C33—Br3	109.7 (4)
C7—C8—H8	120.0	C30—C33—H33A	109.5
C10—C9—C8	120.2 (6)	Br3—C33—H33A	109.5
C10—C9—H9	120.0	C30—C33—H33B	109.5
C8—C9—H9	120.0	Br3—C33—H33B	109.5
C9—C10—C11	120.4 (6)	H33A—C33—H33B	108.5
C9—C10—H10	120.0	C35—C34—C39	121.6 (6)
C11—C10—H10	120.0	C35—C34—O4	118.3 (5)
C12—C11—C10	119.3 (6)	C39—C34—O4	120.1 (5)
C12—C11—H11	120.0	C34—C35—C36	119.5 (6)
C10—C11—H11	120.0	C34—C35—H35	120.0
C11—C12—C7	122.4 (5)	C36—C35—H35	120.0
C11—C12—O2	117.9 (5)	C37—C36—C35	120.1 (7)
C7—C12—O2	119.4 (5)	C37—C36—H36	120.0
C18—C13—C14	120.3 (5)	C35—C36—H36	120.0
C18—C13—O3	121.5 (5)	C36—C37—C38	119.6 (7)
C14—C13—O3	118.0 (5)	C36—C37—C40	120.9 (8)
C15—C14—C13	119.9 (6)	C38—C37—C40	119.5 (8)
C15—C14—H14	120.0	C37—C38—C39	121.2 (7)
C13—C14—H14	120.0	C37—C38—H38	120.0
C14—C15—C16	120.3 (6)	C39—C38—H38	120.0
C14—C15—H15	120.0	C34—C39—C38	118.0 (7)
C16—C15—H15	120.0	C34—C39—H39	120.0
C17—C16—C15	117.9 (5)	C38—C39—H39	120.0
C17—C16—C19	121.8 (6)	C37—C40—Br4	113.3 (5)
C15—C16—C19	120.3 (6)	C37—C40—H40A	109.5
C18—C17—C16	122.7 (6)	Br4—C40—H40A	109.5
C16—C17—H17	120.0	C37—C40—H40B	109.5
C18—C17—H17	120.0	Br4—C40—H40B	109.5
C17—C18—C13	118.9 (5)	H40A—C40—H40B	108.5
C13—C18—H18	120.0	P1—N1—P2	122.0 (3)
C17—C18—H18	120.0	P2—N2—P3	121.5 (2)
C16—C19—Br1	111.9 (4)	P1—N3—P3	121.8 (3)
C16—C19—H19A	109.5	C1—O1—P1	120.4 (3)
Br1—C19—H19A	109.5	C12—O2—P1	120.8 (3)
C16—C19—H19B	109.5	C13—O3—P2	123.0 (3)
Br1—C19—H19B	109.5	C34—O4—P2	120.5 (3)
H19A—C19—H19B	108.5	C20—O5—P3	125.8 (3)
C25—C20—C21	120.0 (5)	C27—O6—P3	120.9 (3)
C25—C20—O5	120.1 (5)	N3—P1—N1	118.0 (2)
C21—C20—O5	119.8 (5)	N3—P1—O1	112.4 (2)
C22—C21—C20	119.1 (6)	N1—P1—O1	105.5 (2)
C22—C21—H21	120.0	N3—P1—O2	105.5 (2)
C20—C21—H21	120.0	N1—P1—O2	112.3 (2)
C21—C22—C23	121.3 (6)	O1—P1—O2	101.99 (18)
C21—C22—H22	120.0	O3—P2—N2	107.0 (2)
C23—C22—H22	120.0	O3—P2—N1	111.9 (2)
C24—C23—C22	118.8 (6)	N2—P2—N1	118.2 (2)
C24—C23—C26	121.0 (7)	O3—P2—O4	99.0 (2)
C22—C23—C26	120.0 (7)	N2—P2—O4	108.9 (2)
C23—C24—C25	121.8 (6)	N1—P2—O4	109.9 (2)
C23—C24—H24	120.0	O5—P3—O6	97.9 (2)
C25—C24—H24	120.0	O5—P3—N2	107.4 (2)
C20—C25—C24	118.9 (6)	O6—P3—N2	109.4 (2)
C20—C25—H25	120.0	O5—P3—N3	111.0 (2)
C24—C25—H25	120.0	O6—P3—N3	111.2 (2)
C23—C26—Br2	112.2 (5)	N2—P3—N3	118.1 (2)
C23—C26—H26A	109.5

O2—P1—O1—C1	−44.8 (4)	C5—C6—C7—C8	−36.7 (8)
N1—P1—O1—C1	−162.3 (4)	C1—C6—C7—C8	143.2 (6)
N3—P1—O1—C1	67.8 (4)	C6—C7—C12—O2	−6.0 (8)
O1—P1—O2—C12	−45.8 (4)	C12—C7—C8—C9	0.1 (8)
N1—P1—O2—C12	66.8 (4)	C8—C7—C12—C11	−0.9 (8)
N3—P1—O2—C12	−163.4 (4)	C6—C7—C12—C11	−179.5 (5)
N3—P1—N1—P2	−2.8 (4)	C8—C7—C12—O2	172.6 (5)
N1—P1—N3—P3	0.5 (4)	C6—C7—C8—C9	178.7 (5)
O1—P1—N3—P3	123.7 (3)	C7—C8—C9—C10	0.9 (9)
O2—P1—N3—P3	−126.0 (3)	C8—C9—C10—C11	−1.2 (10)
O1—P1—N1—P2	−129.4 (3)	C9—C10—C11—C12	0.4 (9)
O2—P1—N1—P2	120.2 (3)	C10—C11—C12—C7	0.7 (9)
N1—P2—O3—C13	−26.9 (5)	C10—C11—C12—O2	−172.9 (5)
O4—P2—O3—C13	88.9 (4)	O3—C13—C14—C15	176.3 (5)
O3—P2—N1—P1	−118.6 (3)	C18—C13—C14—C15	0.8 (9)
N2—P2—O3—C13	−158.0 (4)	O3—C13—C18—C17	−175.6 (5)
O3—P2—O4—C34	179.8 (4)	C14—C13—C18—C17	−0.3 (9)
N1—P2—O4—C34	−62.8 (4)	C13—C14—C15—C16	−2.2 (10)
N2—P2—O4—C34	68.2 (4)	C14—C15—C16—C19	−174.5 (6)
N1—P2—N2—P3	−8.1 (4)	C14—C15—C16—C17	3.0 (9)
N2—P2—N1—P1	6.5 (4)	C15—C16—C17—C18	−2.5 (10)
O3—P2—N2—P3	119.4 (3)	C19—C16—C17—C18	174.9 (6)
O4—P2—N1—P1	132.5 (3)	C15—C16—C19—Br1	−89.6 (7)
O4—P2—N2—P3	−134.4 (3)	C17—C16—C19—Br1	93.1 (7)
N2—P3—O5—C20	−132.4 (5)	C16—C17—C18—C13	1.2 (10)
N3—P3—O5—C20	−2.0 (6)	O5—C20—C21—C22	175.3 (6)
O6—P3—O5—C20	114.4 (5)	O5—C20—C25—C24	−176.5 (5)
O5—P3—N2—P2	132.2 (3)	C21—C20—C25—C24	−0.3 (9)
O6—P3—N2—P2	−122.6 (3)	C25—C20—C21—C22	−0.9 (9)
N3—P3—N2—P2	5.8 (4)	C20—C21—C22—C23	2.2 (10)
O5—P3—O6—C27	159.7 (4)	C21—C22—C23—C24	−2.2 (10)
N2—P3—O6—C27	48.1 (5)	C21—C22—C23—C26	−177.7 (6)
N3—P3—O6—C27	−84.1 (5)	C22—C23—C24—C25	1.0 (9)
O5—P3—N3—P1	−126.6 (3)	C22—C23—C26—Br2	−73.1 (7)
O6—P3—N3—P1	125.6 (3)	C24—C23—C26—Br2	111.5 (6)
N2—P3—N3—P1	−2.0 (4)	C26—C23—C24—C25	176.4 (6)
P1—O1—C1—C2	−108.8 (5)	C23—C24—C25—C20	0.3 (9)
P1—O1—C1—C6	76.9 (6)	C32—C27—C28—C29	2.6 (8)
P1—O2—C12—C7	75.7 (6)	O6—C27—C28—C29	−177.2 (5)
P1—O2—C12—C11	−110.5 (5)	O6—C27—C32—C31	177.7 (5)
P2—O3—C13—C18	−74.7 (6)	C28—C27—C32—C31	−2.1 (8)
P2—O3—C13—C14	109.9 (5)	C27—C28—C29—C30	0.3 (8)
P2—O4—C34—C39	84.1 (6)	C28—C29—C30—C33	176.4 (5)
P2—O4—C34—C35	−97.7 (6)	C28—C29—C30—C31	−3.7 (8)
P3—O5—C20—C21	94.2 (7)	C33—C30—C31—C32	−175.9 (6)
P3—O5—C20—C25	−89.6 (7)	C29—C30—C31—C32	4.1 (9)
P3—O6—C27—C32	−118.7 (5)	C29—C30—C33—Br3	−101.7 (6)
P3—O6—C27—C28	61.1 (7)	C31—C30—C33—Br3	78.3 (7)
O1—C1—C6—C5	171.9 (5)	C30—C31—C32—C27	−1.3 (9)
C6—C1—C2—C3	0.1 (9)	O4—C34—C35—C36	−176.4 (5)
O1—C1—C2—C3	−174.1 (5)	C39—C34—C35—C36	1.8 (10)
O1—C1—C6—C7	−8.0 (8)	O4—C34—C39—C38	176.4 (6)
C2—C1—C6—C5	−2.2 (8)	C35—C34—C39—C38	−1.7 (9)
C2—C1—C6—C7	178.0 (5)	C34—C35—C36—C37	−0.3 (10)
C1—C2—C3—C4	2.4 (9)	C35—C36—C37—C38	−1.2 (11)
C2—C3—C4—C5	−2.6 (10)	C35—C36—C37—C40	179.9 (7)
C3—C4—C5—C6	0.3 (9)	C36—C37—C38—C39	1.3 (11)
C4—C5—C6—C7	−178.2 (5)	C40—C37—C38—C39	−179.8 (7)
C4—C5—C6—C1	1.9 (8)	C36—C37—C40—Br4	96.5 (9)
C1—C6—C7—C12	−38.3 (8)	C38—C37—C40—Br4	−82.5 (8)
C5—C6—C7—C12	141.9 (6)	C37—C38—C39—C34	0.2 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33A···O1ⁱ	0.97	2.60	3.525 (8)	160

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₄₀H₃₂Br₄N₃O₆P₃
M_r	1063.24
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.991 (2), 28.417 (6), 14.008 (3)
β (°)	105.47 (3)
V (Å³)	4216.7 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.98
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker P4 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.392, 0.520
No. of measured, independent and observed [I > 2σ(I)] reflections	52073, 9978, 6049
R_int	0.075
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.192, 1.11
No. of reflections	9978
No. of parameters	505
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.71

Computer programs: XSCANS (Bruker, 2008), SAINT (Bruker, 2008), 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
C33—H33A···O1ⁱ	0.97	2.60	3.525 (8)	160

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.

Acknowledgements

This work was supported by Natural Science Foundation of China (Grant Nos. 20972143, 20602032).

References

Allcock, H. R. (1977). Angew. Chem. Int. Ed. Engl. 16, 147–150. CrossRef PubMed Google Scholar
Allcock, H. R. (2000). Polym. Prep. 14, 553–558. Google Scholar
Bruker (2008). XSCANS, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Manners, I. (1996). Angew. Chem. Int. Ed. Engl. 35, 1602–1607. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Trollsa, M. & Hedrick, J. L. (1998). J. Am. Chem. Soc. 120, 4644–4648. Google Scholar
Wang, L., Ye, Y., Ju, Z., Zhong, S. & Zhao, Y. F. (2009). Phosphorus Sulfur, 184, 1958–1963. CrossRef CAS Google Scholar
Wang, L., Ye, Y., Zhong, S., Zhang, D. & Zhao, Y. F. (2009). Chem. J. Chin. Univ. 30, 493–496 Google Scholar

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

1,1-(Bi­phenyl-2,2′-diyldi­­oxy)-3,3,5,5-tetra­kis­(4-bromo­methyl­phen­­oxy)cyclo­triphosphazene

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,1-(Biphenyl-2,2′-diyldioxy)-3,3,5,5-tetrakis(4-bromomethylphenoxy)cyclotriphosphazene