4,4′,4′′,4′′′-({4′λ5,6λ5,6′λ5-Spiro­[dibenzo[d,f][1,3,2]dioxaphosphepine-6,2′-[1,3,5,2,4,6]tri­aza­triphosphinine]-4′,4′,6′,6′-tetra­yl}tetra­kis­(­oxy))tetra­benzaldehyde

Hou, G.; Zhang, Y.; Zhu, J.; Xiong, A.; Wei, H.; Chu, H.

doi:10.1107/S2414314617017126

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 12| December 2017| x171712

https://doi.org/10.1107/S2414314617017126

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4,4′,4′′,4′′′-({4′λ⁵,6λ⁵,6′λ⁵-Spiro[dibenzo[d,f][1,3,2]dioxaphosphepine-6,2′-[1,3,5,2,4,6]triazatriphosphinine]-4′,4′,6′,6′-tetrayl}tetrakis(oxy))tetrabenzaldehyde

Guohui Hou,^a Yumeng Zhang,^b Jing Zhu,^a ^* Anxian Xiong,^a Hongliang Wei ^a and Huijuan Chu ^a

^aSchool of Chemical Engineering and Environment, Henan University of Technology, Zhengzhou 450001, People's Republic of China, and ^bSchool of Architecture, Sias International University, Zhengzhou 451150, People's Republic of China
^*Correspondence e-mail: zhujing1960@126.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 28 October 2017; accepted 28 November 2017; online 8 December 2017)

The complete molecule of the title compound, C₄₀H₂₈N₃O₁₀P₃, is generated by crystallographic twofold symmetry, with one P and one N atom lying on the rotation axis. The central P₃N₃ ring is close to planar, with an r.m.s. deviation of the six fitted atoms of 0.077 Å. The 2,2′-biphenoxy moiety generates a seven-membered spirocyclic structure with an endocyclic C—C—C—C torsion angle about the central biphenoxy C—C bond of 38.5 (4)°. The formyl-substituted phenyl rings subtend dihedral angles of 56.83 (10) and 61.02 (13)° with respect to the phosphazene core. The C=O and C—H groups of the formyl groups are disordered over two orientations in a 0.640 (4):0.360 (4) ratio. No directional interactions beyond normal van der Waals contacts could be identified in the crystal.

Keywords: crystal structure; cyclotriphosphazene; van der Waals forces.

CCDC reference: 1587896

Structure description

Cyclic phosphazenes are an important family of inorganic ring systems with possible applications as flame retardants, anti-microbial agents, lithium-ion batteries, liquid crystals, organic light emitting diodes, membrane hydrogels, drug carriers, surfactants and phase-transfer catalysts (Uslu et al., 2013 ). The title compound is a new cyclotriphosphazene. Herein, we report its synthesis and crystal structure.

The title compound (Fig. 1), crystallizing in C2/c space group with Z = 4, comprises a cyclotriphosphazene core, a 2,2′-biphenoxy group and four 4-formyl-phenoxy groups. The central phosphazene ring, which is generated by crystallographic twofold symmetry (P1 and N2 lie on the axis) is close to planar, with an r.m.s. deviation of the six fitted atoms of 0.077 Å.

Figure 1
The molecular structure, showing 50% probability displacement ellipsoids (only the major disorder components of the formyl groups are shown).

Incorporation of the 2,2'-biphenoxy moiety at P1 promotes a seven-membered spirocyclic structure with an endocyclic torsion angle about the central biphenoxy C—C bond of 38.5 (4)° for for C6—C5—C5ⁱ—C6ⁱ [symmetry code: (i) 1 − x, y, $[{1\over 2}]$ − z]. The C7 and C14 benzene rings make dihedral angles of 56.83 (10) and 61.02 (13)°, respectively, with the cyclotriphosphazene ring. In the extended structure, there are no directional interactions, the crystal structure being enforced by van der Waals forces only.

Synthesis and crystallization

The title compound was synthesized by two steps: [N₃P₃C_l4(O₂C₁₂H₈)] (T1) was synthesized as previously reported in the literature (Carriedo et al. 1996 ).

A mixture of 4-hydroxybenzaldehyde (2.6816 g, 0.0220 mol) and K₂CO₃ (5.8048 g, 0.0420 mol) in THF (50 ml) was stirred under reflux at room temperature for 0.5 h under nitrogen atmosphere. T1 (2.3047 g, 0.0050 mol) dissolved in 30 ml THF, was added dropwise into the mixture for 1 h at room temperature. The reaction mixture was heated slowly to reflux temperature and then allowed to stir strongly for 6 h. After that, the mixture was filtered twice to remove the white solid that formed. The filtrate was concentrated under vacuum to remove part of the solvent and was poured into a large amount of water to precipitate the crude product, which was recrystallized using a solvent of THF. Colourless prismatic crystals of the title compound were obtained by slow evaporation of the solvent.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. The C=O and C—H moieties of both the C13 and C20 formyl groups are disordered over two overlapping orientations in 0.640 (4):0.360 (4) ratios.

Table 1
Experimental details

Crystal data
Chemical formula	C₄₀H₂₈N₃O₁₀P₃
M_r	803.56
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	32.3691 (16), 10.7492 (2), 13.1332 (7)
β (°)	125.578 (7)
V (Å³)	3716.6 (4)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	2.03
Crystal size (mm)	0.23 × 0.2 × 0.17

Data collection
Diffractometer	Agilent Xcalibur Eos Gemini
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2014 )
T_min, T_max	0.812, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	12837, 3323, 2939
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.143, 1.06
No. of reflections	3323
No. of parameters	262
No. of restraints	13
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.31
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1587896

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314617017126/hb4178sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617017126/hb4178Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617017126/hb4178Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

4,4',4'',4'''-({4'λ⁵,6λ⁵,6'λ⁵-Spiro[dibenzo[d,f][1,3,2]dioxaphosphepine-6,2'-[1,3,5,2,4,6]triazatriphosphinine]-4',4',6',6'-tetrayl}tetrakis(oxy))tetrabenzaldehyde top

Crystal data top

C₄₀H₂₈N₃O₁₀P₃	F(000) = 1656
M_r = 803.56	D_x = 1.436 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 32.3691 (16) Å	Cell parameters from 5579 reflections
b = 10.7492 (2) Å	θ = 4.2–70.6°
c = 13.1332 (7) Å	µ = 2.03 mm⁻¹
β = 125.578 (7)°	T = 293 K
V = 3716.6 (4) Å³	Prism, colourless
Z = 4	0.23 × 0.2 × 0.17 mm

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	3323 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2939 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 16.2312 pixels mm^-1	θ_max = 67.1°, θ_min = 4.4°
ω scans	h = −38→35
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −12→7
T_min = 0.812, T_max = 1.000	l = −15→15
12837 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.047	w = 1/[σ²(F_o²) + (0.0923P)² + 1.510P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.143	(Δ/σ)_max < 0.001
S = 1.06	Δρ_max = 0.43 e Å⁻³
3323 reflections	Δρ_min = −0.31 e Å⁻³
262 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
13 restraints	Extinction coefficient: 0.00127 (14)
Primary atom site location: structure-invariant direct methods

Special details top

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. All C-bound hydrogen atoms were included in calculated positions with C—H = 0.93 Å and allowed to ride, with Uiso(H) = 1.2Ueq(C). DELU and ISOR restraints in SHELXL2014 were applied to atoms C16 and C16. The aldehyde groups at C13 and C20 are disordered over two orientations in 0.640 (4): 0.360 (4) ratios. The disordered O atoms bonded to C13 and C20 were constrained with equal anisotropic displacement parameters.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.39125 (8)	0.3337 (2)	0.0572 (2)	0.0601 (5)
H1	0.3735	0.4044	0.0117	0.072*
C2	0.36550 (9)	0.2259 (2)	0.0461 (2)	0.0666 (6)
H2	0.3302	0.2235	−0.0074	0.080*
C3	0.39210 (9)	0.1229 (2)	0.1142 (3)	0.0656 (6)
H3	0.3748	0.0503	0.1059	0.079*
C4	0.44445 (9)	0.12598 (18)	0.1951 (2)	0.0572 (5)
H4	0.4619	0.0557	0.2421	0.069*
C5	0.47189 (8)	0.23294 (17)	0.20792 (19)	0.0477 (4)
C6	0.44343 (8)	0.33485 (17)	0.13615 (19)	0.0493 (5)
C7	0.54295 (10)	0.7863 (2)	0.5226 (2)	0.0635 (6)
C8	0.56244 (12)	0.6753 (2)	0.5849 (3)	0.0752 (7)
H8	0.5413	0.6076	0.5667	0.090*
C9	0.61402 (15)	0.6669 (3)	0.6748 (3)	0.0913 (9)
H9	0.6279	0.5925	0.7178	0.110*
C10	0.64567 (13)	0.7686 (3)	0.7023 (3)	0.0876 (9)
C11	0.62481 (12)	0.8787 (3)	0.6388 (3)	0.0849 (8)
H11	0.6457	0.9470	0.6571	0.102*
C12	0.57340 (11)	0.8885 (2)	0.5486 (2)	0.0744 (7)
H12	0.5594	0.9629	0.5058	0.089*
C13	0.7014 (2)	0.7618 (6)	0.7995 (5)	0.140 (2)
H13	0.7126	0.6841	0.8371	0.168*	0.640 (4)
H13A	0.7175	0.8360	0.8394	0.168*	0.360 (4)
C14	0.37139 (9)	0.74268 (19)	0.1778 (2)	0.0572 (5)
C15	0.34686 (12)	0.6838 (3)	0.0639 (3)	0.0816 (8)
H15	0.3597	0.6863	0.0164	0.098*
C16	0.30203 (12)	0.6200 (3)	0.0216 (3)	0.0908 (8)
H16	0.2846	0.5794	−0.0552	0.109*
C17	0.28356 (10)	0.6166 (3)	0.0920 (3)	0.0837 (7)
C18	0.30870 (11)	0.6759 (3)	0.2045 (3)	0.0869 (9)
H18	0.2957	0.6737	0.2518	0.104*
C19	0.35297 (10)	0.7389 (3)	0.2488 (3)	0.0726 (7)
H19	0.3703	0.7786	0.3261	0.087*
C20	0.23542 (14)	0.5504 (4)	0.0424 (6)	0.1275 (17)
H20	0.2165	0.5250	−0.0408	0.153*	0.640 (4)
H20A	0.2254	0.5426	0.0956	0.153*	0.360 (4)
N1	0.46628 (6)	0.60788 (16)	0.27931 (18)	0.0562 (5)
N2	0.5000	0.82493 (19)	0.2500	0.0527 (6)
O1	0.46806 (5)	0.44141 (12)	0.13432 (13)	0.0549 (4)
O2	0.49050 (7)	0.79716 (15)	0.43020 (18)	0.0688 (5)
O3	0.41462 (6)	0.81152 (14)	0.2194 (2)	0.0759 (6)
O4	0.7329 (2)	0.8334 (7)	0.8366 (6)	0.165 (2)	0.640 (4)
O4A	0.7238 (4)	0.6851 (13)	0.8270 (10)	0.165 (2)	0.360 (4)
O5	0.21843 (19)	0.5264 (6)	0.1045 (8)	0.173 (2)	0.640 (4)
O5A	0.2100 (4)	0.5091 (10)	−0.0525 (15)	0.173 (2)	0.360 (4)
P1	0.5000	0.53226 (6)	0.2500	0.0489 (2)
P2	0.46970 (2)	0.75408 (4)	0.29196 (6)	0.0529 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0565 (12)	0.0501 (11)	0.0595 (12)	−0.0009 (9)	0.0257 (10)	−0.0006 (9)
C2	0.0550 (12)	0.0647 (14)	0.0738 (14)	−0.0110 (10)	0.0339 (11)	−0.0090 (11)
C3	0.0652 (13)	0.0478 (12)	0.0908 (16)	−0.0157 (10)	0.0492 (13)	−0.0081 (11)
C4	0.0653 (12)	0.0361 (10)	0.0784 (13)	−0.0028 (9)	0.0465 (11)	−0.0009 (9)
C5	0.0555 (11)	0.0335 (9)	0.0588 (11)	−0.0015 (8)	0.0358 (10)	−0.0027 (8)
C6	0.0555 (11)	0.0360 (9)	0.0550 (10)	−0.0052 (8)	0.0313 (9)	−0.0034 (8)
C7	0.0836 (16)	0.0536 (12)	0.0714 (14)	0.0020 (11)	0.0554 (13)	−0.0024 (10)
C8	0.105 (2)	0.0516 (13)	0.0810 (16)	−0.0016 (13)	0.0608 (17)	−0.0017 (11)
C9	0.119 (3)	0.0693 (17)	0.0797 (17)	0.0216 (17)	0.0549 (19)	0.0082 (14)
C10	0.094 (2)	0.091 (2)	0.0702 (16)	0.0075 (17)	0.0433 (16)	−0.0076 (14)
C11	0.093 (2)	0.0838 (19)	0.0741 (16)	−0.0188 (16)	0.0465 (15)	−0.0105 (14)
C12	0.0965 (19)	0.0578 (13)	0.0734 (15)	−0.0053 (13)	0.0520 (15)	0.0009 (11)
C13	0.121 (4)	0.139 (5)	0.118 (3)	0.037 (4)	0.046 (3)	−0.007 (3)
C14	0.0521 (11)	0.0437 (11)	0.0767 (14)	0.0099 (8)	0.0381 (11)	0.0088 (9)
C15	0.0864 (18)	0.0823 (19)	0.0831 (17)	0.0124 (14)	0.0533 (16)	0.0025 (14)
C16	0.0761 (17)	0.0814 (19)	0.0839 (18)	0.0100 (15)	0.0289 (13)	−0.0155 (15)
C17	0.0522 (12)	0.0652 (15)	0.110 (2)	0.0079 (11)	0.0341 (13)	0.0031 (15)
C18	0.0696 (16)	0.097 (2)	0.108 (2)	−0.0019 (15)	0.0602 (17)	0.0059 (18)
C19	0.0632 (14)	0.0820 (18)	0.0752 (15)	−0.0005 (12)	0.0418 (13)	−0.0019 (12)
C20	0.065 (2)	0.092 (3)	0.196 (5)	−0.0006 (18)	0.059 (3)	−0.005 (3)
N1	0.0547 (9)	0.0357 (9)	0.0829 (12)	0.0009 (7)	0.0427 (9)	0.0057 (8)
N2	0.0595 (14)	0.0292 (10)	0.0733 (15)	0.000	0.0409 (12)	0.000
O1	0.0606 (8)	0.0349 (7)	0.0574 (8)	−0.0061 (6)	0.0277 (7)	0.0038 (6)
O2	0.0819 (11)	0.0558 (9)	0.0927 (12)	0.0021 (8)	0.0644 (10)	−0.0036 (8)
O3	0.0621 (10)	0.0417 (8)	0.1282 (16)	0.0085 (7)	0.0579 (11)	0.0123 (8)
O4	0.097 (3)	0.187 (6)	0.139 (4)	−0.012 (3)	0.029 (3)	−0.024 (4)
O4A	0.097 (3)	0.187 (6)	0.139 (4)	−0.012 (3)	0.029 (3)	−0.024 (4)
O5	0.093 (3)	0.149 (4)	0.274 (7)	−0.045 (3)	0.104 (4)	−0.047 (4)
O5A	0.093 (3)	0.149 (4)	0.274 (7)	−0.045 (3)	0.104 (4)	−0.047 (4)
P1	0.0493 (4)	0.0284 (3)	0.0638 (4)	0.000	0.0300 (3)	0.000
P2	0.0546 (4)	0.0330 (3)	0.0794 (4)	0.00327 (18)	0.0436 (3)	0.0026 (2)

Geometric parameters (Å, º) top

C1—H1	0.9300	C13—O4A	1.015 (12)
C1—C2	1.386 (3)	C14—C15	1.374 (4)
C1—C6	1.375 (3)	C14—C19	1.369 (4)
C2—H2	0.9300	C14—O3	1.384 (3)
C2—C3	1.367 (4)	C15—H15	0.9300
C3—H3	0.9300	C15—C16	1.395 (5)
C3—C4	1.381 (3)	C16—H16	0.9300
C4—H4	0.9300	C16—C17	1.363 (5)
C4—C5	1.402 (3)	C17—C18	1.361 (5)
C5—C5ⁱ	1.481 (4)	C17—C20	1.475 (5)
C5—C6	1.388 (3)	C18—H18	0.9300
C6—O1	1.404 (2)	C18—C19	1.371 (4)
C7—C8	1.374 (4)	C19—H19	0.9300
C7—C12	1.380 (4)	C20—H20	0.9300
C7—O2	1.404 (3)	C20—H20A	0.9300
C8—H8	0.9300	C20—O5	1.248 (9)
C8—C9	1.377 (5)	C20—O5A	1.111 (14)
C9—H9	0.9300	N1—P1	1.5776 (18)
C9—C10	1.395 (5)	N1—P2	1.5773 (17)
C10—C11	1.377 (5)	N2—P2ⁱ	1.5732 (11)
C10—C13	1.486 (6)	N2—P2	1.5731 (11)
C11—H11	0.9300	O1—P1	1.5821 (14)
C11—C12	1.375 (4)	O2—P2	1.5943 (19)
C12—H12	0.9300	O3—P2	1.5783 (17)
C13—H13	0.9300	P1—N1ⁱ	1.5776 (18)
C13—H13A	0.9300	P1—O1ⁱ	1.5821 (14)
C13—O4	1.136 (8)

C2—C1—H1	120.4	C15—C14—O3	119.2 (2)
C6—C1—H1	120.4	C19—C14—C15	121.6 (2)
C6—C1—C2	119.1 (2)	C19—C14—O3	119.2 (2)
C1—C2—H2	120.1	C14—C15—H15	121.1
C3—C2—C1	119.8 (2)	C14—C15—C16	117.9 (3)
C3—C2—H2	120.1	C16—C15—H15	121.1
C2—C3—H3	119.7	C15—C16—H16	119.7
C2—C3—C4	120.5 (2)	C17—C16—C15	120.6 (3)
C4—C3—H3	119.7	C17—C16—H16	119.7
C3—C4—H4	119.3	C16—C17—C20	118.7 (4)
C3—C4—C5	121.3 (2)	C18—C17—C16	120.2 (3)
C5—C4—H4	119.3	C18—C17—C20	121.1 (4)
C4—C5—C5ⁱ	120.48 (14)	C17—C18—H18	119.7
C6—C5—C4	116.23 (19)	C17—C18—C19	120.6 (3)
C6—C5—C5ⁱ	123.28 (13)	C19—C18—H18	119.7
C1—C6—C5	122.96 (19)	C14—C19—C18	119.2 (3)
C1—C6—O1	117.06 (18)	C14—C19—H19	120.4
C5—C6—O1	119.77 (18)	C18—C19—H19	120.4
C8—C7—C12	122.0 (3)	C17—C20—H20	117.8
C8—C7—O2	119.5 (2)	C17—C20—H20A	116.9
C12—C7—O2	118.6 (2)	O5—C20—C17	124.4 (6)
C7—C8—H8	120.8	O5—C20—H20	117.8
C7—C8—C9	118.4 (3)	O5A—C20—C17	126.3 (8)
C9—C8—H8	120.8	O5A—C20—H20A	116.9
C8—C9—H9	119.6	P2—N1—P1	121.54 (11)
C8—C9—C10	120.8 (3)	P2—N2—P2ⁱ	122.09 (14)
C10—C9—H9	119.6	C6—O1—P1	123.20 (13)
C9—C10—C13	121.7 (4)	C7—O2—P2	117.22 (14)
C11—C10—C9	119.3 (3)	C14—O3—P2	123.85 (13)
C11—C10—C13	119.0 (4)	N1—P1—N1ⁱ	117.97 (13)
C10—C11—H11	119.7	N1—P1—O1ⁱ	104.01 (9)
C12—C11—C10	120.6 (3)	N1ⁱ—P1—O1ⁱ	113.21 (9)
C12—C11—H11	119.7	N1ⁱ—P1—O1	104.01 (9)
C7—C12—H12	120.5	N1—P1—O1	113.21 (9)
C11—C12—C7	119.0 (3)	O1ⁱ—P1—O1	103.77 (10)
C11—C12—H12	120.5	N1—P2—O2	111.51 (10)
C10—C13—H13	113.8	N1—P2—O3	109.93 (9)
C10—C13—H13A	116.4	N2—P2—N1	117.73 (10)
O4—C13—C10	132.3 (7)	N2—P2—O2	108.79 (8)
O4—C13—H13	113.8	N2—P2—O3	108.35 (8)
O4A—C13—C10	127.1 (9)	O3—P2—O2	98.85 (11)
O4A—C13—H13A	116.4

C1—C2—C3—C4	0.8 (4)	C13—C10—C11—C12	−179.8 (3)
C1—C6—O1—P1	114.63 (19)	C14—C15—C16—C17	−0.2 (4)
C2—C1—C6—C5	−1.2 (4)	C14—O3—P2—N1	14.2 (2)
C2—C1—C6—O1	173.4 (2)	C14—O3—P2—N2	144.1 (2)
C2—C3—C4—C5	−1.5 (4)	C14—O3—P2—O2	−102.7 (2)
C3—C4—C5—C5ⁱ	−178.0 (2)	C15—C14—C19—C18	−0.7 (4)
C3—C4—C5—C6	0.8 (3)	C15—C14—O3—P2	−85.2 (3)
C4—C5—C6—C1	0.6 (3)	C15—C16—C17—C18	0.2 (5)
C4—C5—C6—O1	−173.89 (18)	C15—C16—C17—C20	178.6 (3)
C5ⁱ—C5—C6—C1	179.3 (2)	C16—C17—C18—C19	−0.5 (5)
C5ⁱ—C5—C6—O1	4.8 (3)	C16—C17—C20—O5	169.7 (5)
C5—C6—O1—P1	−70.6 (2)	C16—C17—C20—O5A	−6.1 (10)
C6—C1—C2—C3	0.5 (4)	C17—C18—C19—C14	0.7 (4)
C6—O1—P1—N1ⁱ	162.08 (16)	C18—C17—C20—O5	−11.9 (6)
C6—O1—P1—N1	−68.66 (17)	C18—C17—C20—O5A	172.4 (9)
C6—O1—P1—O1ⁱ	43.44 (13)	C19—C14—C15—C16	0.4 (4)
C7—C8—C9—C10	0.1 (4)	C19—C14—O3—P2	97.3 (3)
C7—O2—P2—N1	77.14 (18)	C20—C17—C18—C19	−178.9 (3)
C7—O2—P2—N2	−54.33 (18)	O2—C7—C8—C9	179.8 (2)
C7—O2—P2—O3	−167.25 (16)	O2—C7—C12—C11	−179.9 (2)
C8—C7—C12—C11	0.5 (4)	O3—C14—C15—C16	−177.0 (2)
C8—C7—O2—P2	−85.8 (2)	O3—C14—C19—C18	176.7 (2)
C8—C9—C10—C11	0.4 (5)	P1—N1—P2—N2	11.19 (17)
C8—C9—C10—C13	179.7 (4)	P1—N1—P2—O2	−115.56 (14)
C9—C10—C11—C12	−0.5 (5)	P1—N1—P2—O3	135.85 (14)
C9—C10—C13—O4	−178.3 (8)	P2—N1—P1—N1ⁱ	−5.75 (9)
C9—C10—C13—O4A	28.3 (14)	P2—N1—P1—O1	−127.48 (12)
C10—C11—C12—C7	0.0 (4)	P2—N1—P1—O1ⁱ	120.57 (13)
C11—C10—C13—O4	1.0 (10)	P2ⁱ—N2—P2—N1	−5.44 (8)
C11—C10—C13—O4A	−152.4 (12)	P2ⁱ—N2—P2—O2	122.61 (8)
C12—C7—C8—C9	−0.6 (4)	P2ⁱ—N2—P2—O3	−130.89 (9)
C12—C7—O2—P2	94.5 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Acknowledgements

We would like to thank Ms Y. Zhu for technical assistance.

Funding information

Funding for this research was provided by: the Science and Technology Hall of Henan Province (award No. No. 162102210038); the Science and Technology Bureau of Zheng-zhou City (award No. No. 20150250).

References

Agilent (2014). CrysAlisPro. Agilent Technolgies Ltd, Yarnton, England. Google Scholar
Carriedo, G. A., Fernández-Catuxo, L., Alonso, F. J. G., Gómez-Elipe, P. & González, P. A. (1996). Macromolecules, 29, 5320–5325. CrossRef CAS Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Uslu, A., Ün, Ş. Ş., Kılıç, A., Yılmaz, Ş., Yuksel, F. & Hacıvelioğlu, F. (2013). Inorg. Chim. Acta, 405, 140–146. Web of Science CSD CrossRef CAS Google Scholar

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