The crystal structure of four phosphorus-containing polyoxamacrocycles

Article abstract of DOI:10.1080/10426507.2013.829834

The crystal structures of four phosphorus-containing polyoxamacrocycles 2,4, 6,11,13-Pentachloro-dibenzo[d,g][1,3,9,2]trioxaphosphacycloundecan-2-thione (1),2,4,9,14, 16-Pentachloro-dibenzo[g,j][1,3,6,12,2]tetraoxaphosphacyclotetra- decan-2-thione (2), 2,4, 10,16,18-Pentachloro-dibenzo[h,k][1,3,7,12,2]tetraoxa- phosphacyclohexadecan-2-thione (3) and 2,4,6,12,14,18,20,28,30 - Nona-chloro-tetrabenzo[d,g,p,s] [1,3,9,13,15,21,2,14]hexaoxa diphosphacyclotetracosan-2,14-dithione (4) have been determined by X-ray diffraction. The result shows that compound 4 has a center of symmetry, and compounds 1, 2, and 3 have no elements of symmetry. The molecules of compounds 2 and 4 form inclusion complex with neutral molecule guest (CHCl₃) which is outside of the phosphorus-containing macrocycle in the ratio of 1:1, and compounds 1 and 3 do not form inclusion complexes with CHCl₃. The result obtained in this paper lays a foundation for further research on the complexing properties of phosphorus-containing polyoxamacrocycles. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional text, figures, and tables.]

Full text of DOI:10.1080/10426507.2013.829834

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The Crystal Structure of
Four Phosphorus-Containing
Polyoxamacrocycles
Xiao Mei Zhang a b , Yan Hong Dong a , Wan Yi Chen a & Dao Quan
Wang a
a Department of Applied Chemistry , China Agricultural University ,
Beijing , 100193 , People's Republic of China
b College of Chem. and Eng. , Anhui University of Science and
Technology , Huainan , Anhui , 232001 , People's Republic of China
Accepted author version posted online: 20 Aug 2013.Published
online: 12 Mar 2014.
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To cite this article: Xiao Mei Zhang , Yan Hong Dong , Wan Yi Chen & Dao Quan Wang (2014) The
Crystal Structure of Four Phosphorus-Containing Polyoxamacrocycles, Phosphorus, Sulfur, and Silicon
and the Related Elements, 189:4, 503-510, DOI: 10.1080/10426507.2013.829834
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Phosphorus, Sulfur, and Silicon, 189:503–510, 2014
Copyright ꢀC Taylor & Francis Group, LLC
ISSN: 1042-6507 print / 1563-5325 online
DOI: 10.1080/10426507.2013.829834
THE CRYSTAL STRUCTURE OF FOUR
PHOSPHORUS-CONTAINING POLYOXAMACROCYCLES
Xiao Mei Zhang,1,2 Yan Hong Dong,1 Wan Yi Chen,1
and Dao Quan Wang1
1Department of Applied Chemistry, China Agricultural University, Beijing 100193,
People’s Republic of China
2College of Chem. and Eng., Anhui University of Science and Technology,
Huainan, Anhui, 232001, People’s Republic of China
GRAPHICAL ABSTRACT
Abstract The crystal structures of four phosphorus-containing polyoxamacrocycles 2,4,
6,11,13-Pentachloro-dibenzo[d,g][1,3,9,2]trioxaphosphacycloundecan-2-thione (1),2,4,9,14,
16-Pentachloro-dibenzo[g,j][1,3,6,12,2]tetraoxaphosphacyclotetra-decan-2-thione (2), 2,4,
10,16,18-Pentachloro-dibenzo[h,k][1,3,7,12,2]tetraoxa-phosphacyclohexadecan-2-thione (3)
and 2,4,6,12,14,18,20,28,30—Nona-chloro-tetrabenzo[d,g,p,s] [1,3,9,13,15,21,2,14]hexaoxa
diphosphacyclotetracosan-2,14-dithione (4) have been determined by X-ray diffraction. The
result shows that compound 4 has a center of symmetry, and compounds 1, 2, and 3 have
no elements of symmetry. The molecules of compounds 2 and 4 form inclusion complex with
neutral molecule guest (CHCl3) which is outside of the phosphorus-containing macrocycle
in the ratio of 1:1, and compounds 1 and 3 do not form inclusion complexes with CHCl3.
The result obtained in this paper lays a foundation for further research on the complexing
properties of phosphorus-containing polyoxamacrocycles.
[Supplementary materials are available for this article. Go to the publisher’s online edition of
Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental
files: Additional text, figures, and tables.]
Keywords Crystal structure; phosphorus-containing macrocycle; inclusion complex
Received 25 April 2013; accepted 22 July 2013.
Address correspondence to Dr Daoquan Wang, Department of Applied Chemistry, China Agricultural
University, Beijing 100193, People’s Republic of China. E-mail: wangdq@cau.edu.cn
503

504
X. M. ZHANG ET AL.
INTRODUCTION
A great deal of attention has been paid to the synthesis and chemistry of phosphorus-
containing macrocycles in recent years1–6 due to their complexing ability, molecular
recognizing ability, and their bioactivity. The size of the holes formed by macrocycles,
and the type and number of heteroatoms are important factors that influence their
complexing and recognizing properties. We reported the synthesis, bioactivity, and
complexing property of substituted dibenzo [1, 3, 2]-dioxaphosphocins.7–10 One of the
interesting phenomina we observed in our work is that some of these eight-membered
compounds easily form complexes with some solvents. In view of the property of
phosphane oxides serving as strong hydrogen-bond acceptors and as a continuation of
our work, we intend to increase the size of the cycle and the number of oxygen atom
based on the dibenzo [1, 3, 2]-dioxaphosphocin to improve their complexing ability.
We reported the synthesis of four phosphorus-containing polyoxamacrocycles with
one or two reactive thiophosphoryl chloride groups, namely, 2,4,6,11,13-Pentachloro-
dibenzo[d,g][1,3,9,2]trioxaphosphacycloundecan-2-thione (1), 2,4,9,14,16-Penta- chlorod-
ibenzo[g,j][1,3,6,12,2]tetraoxaphosphacyclotetradecan-2-thione (2), 2,4,10,16,18-Penta-
chlorodibenzo[h,k][1,3,7,12,2]tetraoxaphosphacyclohexadecan-2-thione (3), and 2,4,6,12,
14,18,20,28,30-Nonachlorotetrabenzo[d,g,p,s] [1,3,9,13,15,21,2,14]hexaoxadiphosphacyc
lotetracosan-2,14-dithione (4) by introducing CH2CH2O or CH2CH2CH2O units into
bis(3,5-dichloro-2-hydroxylphenyl)methan, followed by reaction with thiophosphoryl
chloride,11 and retaining reactive thiophosphoryl chloride groups to benefit their derivation.
In this paper, we would like to report their crystal structures.

CRYSTAL STRUCTURE OF FOUR PHOSPHORUS-CONTAINING POLYOXAMACROCYCLES 505
Table 1 Crystal structures and data refinement parameters for the compounds 1, 2, 3, and 4
Compounds
1
2
3
4
Empirical
formula
C15H10Cl5O3PS
C17H14Cl5O4PS·
CHCl3
C19H18Cl5O4PS
C32H24Cl10O6P2S2·
CHCl3
Formula weight
478.54
641.97
550.65
1104.52
Crystal system/
Triclinic/P-1
Monoclinic/P2(1)/n
Monoclinic/P2(1)/c
Triclinic/P-1
Space group
a/Å
b/Å
8.8145(10)
10.8876(10)
11.8022(10)
101.863(7)
111.921(2)
108.376(4)
927.52(16)
1
14.9760(5)
9.1188(4)
18.0492(9)
90
91.609(2)
90
12.3919(6)
13.6990(5)
14.0032(6)
90
100.369(2)
90
8.3269(6)
9.8261(7)
15.8216(10)
94.680(2)
102.939(4)
94.898(2)
1250.28(15)
2
c/Å
α/◦
β/◦
γ /◦
V/Å3
2463.88(18)
4
2338.31(17)
4
Z
Dcalc (g/cm3)
1.713
0.994
1.731
1.090
1.564
0.803
1.623
1.066
μ (mm−1
)
Crystal size
(mm)
0.48 × 0.29 × 0.15
0.41 × 0.24 × 0.19
0.38 × 0.34 × 0.12
0.55 × 0.37 × 0.34
Color/shape
Temp (K)
Theta range for
collection/◦
Reflections
collected
Colorless/flaky
293(2)
2.32 to 27.36
Colorless/flaky
293(2)
2.26 to 27.43
Colorless/flaky
293(2)
2.10 to 27.46
Colorless/flaky
293(2)
2.09 to 27.41
5963
9919
10038
8778
Independent
reflections
Data/restraints/
parameters
Goodness of fit
on F2
3976 [R(int) =
0.0330]
3976/0/226
5442 [R(int) =
0.0278]
5442/0/290
5279 [R(int) =
0.0651]
5279/0/271
5511 [R(int) =
0.0326]
5511/0/272
0.968
0.786
0.547
0.863
Final R indices
[I > 2σ(I)]
R indices (all
data)
R1 = 0.0292, wR2
= 0.0727
R1 = 0.0256, wR2
= 0.0400
R1 = 0.0341, wR2
= 0.0323
R1 = 0.0484, wR2 =
0.1239
R1 = 0.0388, wR2
= 0.0746
R1 = 0.0476, wR2
= 0.0418
R1 = 0.1940, wR2
= 0.0399
R1 = 0.1043, wR2 =
0.1353
Largest
0.397 and −0.298
0.338 and −0.334
0.256 and −0.285
0.624 and −0.412
difference
peak/hole (e.
Å3)
RESULTS AND DISCUSSION
Crystal structures and Data refinement parameters for the compounds 1, 2, 3, and 4
are summarized in Table 1, The crystal of compound 1 belongs to the triclinic system, space
group P-1 with a = 8.8145(10), b = 10.8876(10), c = 11.8022(10) Å, α = 101.863(7),
β = 111.921(2), γ = 108.376(4)◦. The crystal of compound 2 belongs to the monoclinic
system, space group P2(1)/n with a = 14.9760(5), b = 9.1188(4), c = 18.0492(9) Å, α =
90, β = 91.609(2), γ = 90◦. The crystal of compound 3 belongs to the monoclinic system,
space group P2(1)/c with a = 12.3919(6), b = 13.6990(5), c = 14.0032(6) Å, α = 90,
β = 100.369(2), γ = 90◦. The crystal of compound 4 belongs to the triclinic system, space
group P-1 with a = 8.3269(6), b = 9.8261(7), c = 15.8216(10) Å, α = 94.680(2), β =
102.939(4), γ = 94.898(2)◦.

506
X. M. ZHANG ET AL.
Figure 1 Crystal structure of compound 1.
The selected bond lengths and bond angles for the compounds 1, 2, 3, and 4 are listed
in Tables 2–5 respectively, and the crystal structures of compounds 1, 2, 3, and 4 revealed
in Figures 1–4 respectively.
Table 2 Selected bond lengths (Å) and bond angles (◦) for the compound 1
Bond
Dist.
Bond
Dist.
Bond
Dist.
P(1)–O(2)
P(1)–O(1)
P(1)–S(1)
P(1)–Cl(5)
O(1)–C(13)
Angle
1.5617(13)
1.5976(13)
1.8978(7)
2.0045(7)
1.399(2)
(◦)
O(2)–C(14)
O(3)–C(1)
O(3)–C(15)
C(1)–C(6)
C(6)–C(7)
1.466(2)
1.374(2)
1.441(2)
1.402(2)
1.520(2)
(◦)
C(7)–C(8)
C(8)–C(13)
C(14)–C(15)
1.518(2)
1.381(3)
1.494(3)
Angle
Angle
(◦)
O(2)-P(1)-O(1)
O(2)-P(1)-S(1)
O(1)-P(1)-S(1)
O(2)-P(1)-Cl(5)
O(1)-P(1)-Cl(5)
S(1)-P(1)-Cl(5)
104.80(7)
112.72(6)
118.17(5)
104.04(6)
98.91(5)
116.28(3)
C(13)-O(1)-P(1)
C(14)-O(2)-P(1)
C(1)-O(3)-C(15)
O(3)-C(1)-C(6)
O(3)-C(1)-C(2)
C(6)-C(1)-C(2)
124.29(12)
123.16(12)
117.92(14)
118.22(16)
123.28(16)
118.30(16)
C(1)–C(6)–C(7)
C(8)–C(7)–C(6)
C(13)–C(8)–C(7)
C(8)–C(13)–O(1)
O(2)–C(14)–C(15)
O(3)–C(15)–C(14)
119.14(16)
113.90(15)
120.73(16)
118.81(16)
108.54(15)
113.95(15)

CRYSTAL STRUCTURE OF FOUR PHOSPHORUS-CONTAINING POLYOXAMACROCYCLES 507
Figure 2 Crystal structure of compound 2.
Crystal structures of compounds 1, 2, and 3 (Figures 1–3 and Tables 2–4) show that
two phenyl rings are approximately perpendicular to each other and there are no elements of
symmetry in the molecules. It is safe to predict that compounds 1, 2, and 3 can exist in two
enantiomeric forms. Crystal structure of compound 4 (Figure 4 and Table 5) shows that it
has a center of symmetry which is the centre of the phosphorus-containing macrocycle and
is therefore optically inactive although two phenyl rings are approximately perpendicular
to each other in two phenyl-methylene-phenyl units.
Table 3 Selected bond lengths (Å) and bond angles (◦) for the compound 2
Bond
Dist.
Bond
Dist.
Bond
Dist.
S(1)–P(1)
P(1)–O(2)
P(1)–O(1)
P(1)–Cl(1)
O(1)–C(1)
O(2)–C(17)
Angle
1.9078(7)
1.5704(12)
1.5720(12)
2.0125(6)
1.4591(19)
1.4583(19)
(◦)
O(3)–C(15)
O(3)–C(16)
O(4)–C(3)
O(4)–C(2)
C(1)–C(2)
1.374(2)
1.440(2)
1.389(2)
1.4481(19)
1.495(2)
C(8)–C(9)
C(9)–C(10)
C(10)–C(15)
C(16)–C(17)
1.504(2)
1.522(2)
1.402(2)
1.491(2)
C(3)–C(8)
Angle
1.396(2)
(◦)
Angle
(◦)
O(2)–P(1)–O(1)
O(2)–P(1)–S(1)
O(1)–P(1)–S(1)
O(2)–P(1)–Cl(1)
O(1)–P(1)–Cl(1)
S(1)-P(1)-Cl(1)
C(1)-O(1)-P(1)
102.44(6)
118.71(5)
116.91(5)
99.71(5)
102.45(5)
113.99(3)
120.28(10)
C(17)–O(2)–P(1)
C(15)–O(3)–C(16)
C(3)–O(4)–C(2)
O(1)–C(1)–C(2)
O(4)–C(2)–C(1)
C(4)–C(3)–C(8)
O(4)–C(3)–C(8)
122.93(11)
113.59(12)
114.86(12)
108.27(14)
108.82(14)
120.28(16)
117.95(15)
C(3)–C(8)–C(9)
C(8)–C(9)–C(10)
C(15)–C(10)–C(9)
O(3)–C(15)–C(10)
O(3)–C(16)–C(17)
O(2)–C(17)–C(16)
120.52(16)
112.65(14)
120.33(16)
120.90(15)
106.89(14)
109.66(14)

508
X. M. ZHANG ET AL.
Figure 3 Crystal structure of compound 3.
Figure 4 Crystal structure of compound 4.

CRYSTAL STRUCTURE OF FOUR PHOSPHORUS-CONTAINING POLYOXAMACROCYCLES 509
Table 4 Selected bond lengths (Å) and bond angles (◦) for the compound 3
Bond
Dist.
Bond
Dist.
Bond
Dist.
P(1)–O(4)
P(1)–O(3)
P(1)–S(1)
P(1)–Cl(5)
O(1)–C(1)
O(1)–C(19)
Angle
1.553(2)
1.5594(19)
1.9078(13)
1.9785(13)
1.371(3)
1.452(3)
(◦)
O(2)–C(13)
O(2)–C(14)
O(3)–C(16)
O(4)–C(17)
C(1)–C(6)
C(6)–C(7)
Angle
1.372(3)
1.434(3)
1.458(3)
1.443(3)
1.391(4)
1.516(4)
(◦)
C(7)–C(8)
C(8)–C(13)
1.510(3) 1.387(4)
1.493(3) 1.517(3)
1.441(4) 1.451(3)
C(14)–C(15)
C(15)–C(16)
C(17)–C(18)
C(18)–C(19)
Angle
(◦)
O(4)–P(1)–O(3)
O(4)–P(1)–S(1)
O(3)–P(1)–S(1)
O(4)–P(1)–Cl(5)
O(3)–P(1)–Cl(5)
S(1)–P(1)–Cl(5)
C(1)–O(1)–C(19)
C(13)–O(2)–C(14)
101.98(12) C(16)–O(3)–P(1) 120.93(19)
C(13)–C(8)–C(7)
O(2)–C(13)–C(8)
O(2)–C(14)–C(15) 105.9(2) 110.8(3)
C(14)–C(15)–C(16) 120.3(4) 109.7(3)
O(3)–C(16)–C(15)
C(18)–C(17)–O(4)
C(17)–C(18)–C(19)
C(18)–C(19)–O(1)
120.1(4) 117.9(4)
109.8(3) 114.7(3)
115.62(11) C(17)–O(4)–P(1)
111.32(10) O(1)–C(1)–C(6)
106.38(10) O(1)–C(1)–C(2)
107.50(10) C(3)–C(2)–Cl(1)
123.5(2)
119.5(4)
120.5(4)
119.5(3)
117.5(4)
119.4(3)
114.5(3)
113.16(7)
114.3(2)
115.9(3)
C(4)–C(3)–C(2)
C(1)–C(6)–C(7)
C(8)–C(7)–C(6)
It can also be seen from Figures 2 and 4 that the molecules of compounds 2 and 4 form
inclusion complex with neutral molecule guest (CHCl3) which is outside of the phosphorus-
containing macrocycle in the ratio of 1:1 using CHCl3 as crystallization solvent. The reason
why compounds 1 and 3 did not form inclusion complex with CHCl3 is not clear. The further
work is needed.
EXPERIMENTAL
Preparation of Compounds 1, 2, 3, and 4
(3,5-Dichloro-2-hydroxyphenyl) (3,5-dichloro-2-hydroxyethoxyphenyl)-methane
and bis(3,5-dichloro-2-hydroxyethoxyphenyl)methane, prepared starting from bis(3,5-
Dichloro-2-hydroxyphenyl)methane by reaction with chloroacetic ester followed by
Table 5 Selected bond lengths (Å) and bond angles (◦) for the compound 4
Bond
Dist.
Bond
Dist.
Bond
Dist.
Cl(5)–P(1)
P(1)–O(3)#1
P(1)–O(1)
P(1)–S(1)
O(1)–C(1)
1.9924(14)
1.568(3)
1.582(2)
O(2)–C(13)
O(2)–C(14)
O(3)–C(16)
O(3)–P(1)#1
C(6)–C(7)
1.376(4)
1.449(4)
1.437(5)
1.568(3)
1.511(4)
(◦)
C(7)–C(8)
C(14)–C(15)
C(15)–C(16)
1.511(5)
1.482(5)
1.498(6)
1.8835(14)
1.396(4)
Angle
(◦)
Angle
Angle
(◦)
O(3)#1–P(1)–O(1)
O(3)#1–P(1)–S(1)
O(1)–P(1)–S(1)
O(3)#1–P(1)–Cl(5)
O(1)–P(1)–Cl(5)
S(1)–P(1)-Cl(5)
99.87(13)
118.76(14)
117.25(10)
102.68(13)
101.06(10)
114.49(7)
C(1)–O(1)–P(1)
C(13)–O(2)–C(14)
C(16)–O(3)–P(1)#1
C(2)–C(1)–C(6)
C(6)–C(1)–O(1)
C(1)–C(6)–C(7)
123.10(19)
113.5(3)
122.0(3)
121.2(3)
119.7(3)
120.5(3)
C(8)–C(7)–C(6)
C(13)–C(8)–C(7)
O(2)–C(13)–C(8)
O(2)–C(14)–C(15)
C(14)–C(15)–C(16)
O(3)–C(16)–C(15)
113.8(3)
120.4(3)
119.1(3)
109.8(3)
117.2(4)
106.6(4)
Symmetry transformations used to generate equivalent atoms: #1 −x, −y, −z + 1.

510
X. M. ZHANG ET AL.
reduction with lithium aluminum hydride, were allowed to react with thiophos-
phoryl chloride to give two-component cyclization products 1 and 2 respectively.
Bis(3,5-dichloro-2-hydroxypropoxyphenyl)methane and (3,5-Dichloro-2-hydroxyphenyl)
(3,5-dichloro-2-hydroxypropoxyphenyl)methane, prepared starting from bis(3,5-Dichloro-
2-hydroxyphenyl)methane by reaction with 3-bromopropene followed by hydroboration,
were allowed to react with thiophosphoryl chloride to give two-component cyclization
product 3 and four-component cyclization product 4 respectively (for detailed synthetic
route, see ref. 11).
X-Ray Crystal Structure Determination of Compounds 1, 2, 3, and 4
The crystals of compounds 1, 2, 3, and 4 were obtained respectively by slow evapo-
ration of a solution of chloroform.
All measurements were made with a Rigaku R-axis RAPID IP four circle area
detector using graphite monochromatized Mo Kα (λ = 0.071073 nm) radiation at 293 K.
The structures were solved by direct methods using SHELX, and refined on F2 using all
data by full-matrix least-squares procedures with SHELXL-97. All nonhydrogen atoms
were refined with anisotropic displacement parameters. An empirical absorption correction
based on Xscans was made on all data. Hydrogen atoms were located from the difference
map and were constrained to geometrical estimates. Final refinement was carried out with
isotropic displacement parameters applied to hydrogen atoms.
SUPPORTING INFORMATION
CCDC 894570 (compound 4), CCDC 894571 (compound 2), CCDC 894573 (com-
pound 1), and CCDC 894574 (compound 3) contain the supplementary crystallographic
data for this paper. These data can be obtained free of charge from the Cambridge Crystal-
lographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; Telephone: (44) 01223
762910; e-mail: deposit@ccdc.cam.ac.uk
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