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Acta Crystallographica Section E: Crystallographic Communications logoLink to Acta Crystallographica Section E: Crystallographic Communications
. 2016 Jan 13;72(Pt 2):174–177. doi: 10.1107/S2056989015024780

Crystal structure of (n-but­yl)[2-(2,6-di­meth­oxy­phen­yl)-6-methyl­phen­yl](2-meth­oxy­phen­yl)phospho­nium chloride monohydrate

Ge Feng a, Alexander S Filatov a, Richard F Jordan a,*
PMCID: PMC4770974  PMID: 26958381

In a phospho­nium chloride hydrated salt containing four different substituents (H, alkyl, aryl, and biar­yl) on the P atom, the Cl− ions and water mol­ecules are linked by pairs of Owater—H⋯Cl− hydrogen bonds and further linked to the phospho­nium cation by P—H+⋯Cl− and CAr/OMe—H⋯Owater hydrogen bonds to form an infinite one-dimensional chain along the [010] direction.

Keywords: crystal structure, phospho­nium salt, hydrogen bonding

Abstract

The title hydrated salt, C26H32O3P+·Cl−·H2O, contains four different substit­uents (H, alkyl, aryl, and biar­yl) on the P atom. The P—H hydrogen atom of the phospho­nium ion was located in a difference Fourier map and refined without imposing additional restraints. In the crystal, the Cl− ions and water mol­ecules are linked by pairs of Owater—H⋯Cl− hydrogen bonds and further linked to the phospho­nium cation by P—H+⋯Cl− and CAr/OMe—H⋯Owater hydrogen bonds to form an infinite one-dimensional chain along the [010] direction.

Chemical context  

Palladium(II) alkyl complexes that contain ortho-phosphino-arene­sulfonate ligands ([PO]−) exhibit unique behavior in olefin polymerization (Nakamura et al., 2009 ▸; Ito & Nozaki, 2010 ▸; Nakamura et al., 2013 ▸). One of the main drawbacks of traditional (PO)Pd alkyl catalysts is that they produce polyethyl­ene with only low-to-moderate mol­ecular weight (Drent et al., 2002 ▸; Vela et al., 2007 ▸). Studies have shown that incorporating bulky substituents on phospho­rous in the [PO]− ligand is an effective strategy to increase the mol­ecular weight of the produced polymer (Skupov et al., 2007 ▸; Shen & Jordan, 2009 ▸; Ota et al., 2014 ▸). Therefore we were inter­ested in developing the new [PO]− ligand 2 that contains bulky P-substituents (see Scheme). We attempted to prepare 2 by the reaction of (2-{2,6-(OMe)2-Ph}-6-Me-Ph)(2-OMe-Ph)PCl (3) with in situ-generated dili­thia­ted benzene­sulfonate to generate 2′, followed by acidification with HCl. However, this procedure did not afford 2 but rather produced [(2-{2,6-(OMe)2-Ph}-6-Me-Ph)(2-OMe-Ph)(n-Bu)PH]Cl (1) in low yield after workup, which crystallizes as the monohydrate 1·H2O (I). 1 likely formed by the reaction of 3 with the slight excess of n-BuLi present in the dili­thia­ted benzene­sulfonate solution. Here we report the crystal structure of I.graphic file with name e-72-00174-scheme1.jpg

Structural commentary  

Crystals of 1·H2O (I) suitable for X-ray diffraction analysis were obtained by recrystallization from wet CH2Cl2/Et2O (Fig. 1 ▸ a). The P—C bond lengths are almost equal for the alkyl, aryl, and biaryl substituents [1.7994 (14), 1.7824 (14), and 1.8043 (13) Å, respectively]. The C—P—H angles are also very similar [106.2 (7), 104.9 (7), and 107.5 (7)° for the alkyl, aryl, and biaryl substituents, respectively]. The aryl rings in the biaryl unit are essentially perpendicular to each other, with the angle between the mean planes passing through the six-membered rings being 88.60 (6)°. This conformation minimizes steric inter­actions between the ortho-meth­oxy groups and the ortho-hydrogens on the two rings. The mean planes passing through 2,6-di­meth­oxy­phenyl ring and the C-atoms of the 2-meth­oxy­phenyl and n-butyl groups are almost parallel to each other [the angle is 10.36 (5)°, Fig. 1 ▸ b]. The P—H hydrogen atom was located in a difference Fourier map and refined without additional restraints. The refined P—H bond length of 1.313 (16) Å is similar to those previously reported (Burke et al., 2000 ▸, Zhu et al., 2007 ▸, Wucher et al., 2013 ▸).

Figure 1.

Figure 1

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(a) The mol­ecular structure of I drawn with the 50% probability ellipsoids and showing the atom-labelling scheme. (b) A different view of I with H2O and Cl− moieties omitted for clarity.

Supra­molecular features  

The P—H+, Cl−, and water mol­ecule are involved in inter­molecular hydrogen bonding (Fig. 2 ▸, Table 1 ▸). Two Cl− ions and two water mol­ecules form a rhombus (Fig. 3 ▸) in which the O⋯Cl distances are almost equal [3.1717 (13) and 3.1841 (13) Å]. The Cl− ions are further engaged in P—H+⋯Cl− hydrogen bonds [2.523 (16) Å], and the water mol­ecules are also involved in CAr/OMe—H⋯Owater contacts [2.243 (16) and 2.254 (16) Å], forming infinite chains along the [010] direction (Fig. 3 ▸). The involvement of the P—H hydrogen atom in hydrogen bonding stands in contrast to what has been observed in some related structures. For example, in the structures of tri­phenyl­phospho­nium perchlorate (Zhu et al., 2007 ▸) and tris­(ortho-tol­yl)phospho­nium tetra­chloro­borate (Burke et al., 2000 ▸), there is no evidence for involvement of the P—H hydrogen atom in hydrogen bonding.

Figure 2.

Figure 2

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Hydrogen bonds in I. [Symmetry codes: (i) x − 1, y + 1, z; (ii) −x + 1, −y, −z + 1; (iii) x − 1, y, z.]

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
P1—H1P⋯Cl1i 1.313 (16) 2.523 (16) 3.5798 (5) 135.5 (10)
C21—H21⋯O4 0.95 2.53 3.4594 (19) 167
C26—H26C⋯O4 0.98 2.53 3.2250 (19) 128
O4—H4X⋯Cl1ii 0.93 (2) 2.24 (2) 3.1717 (13) 173 (2)
O4—H4Y⋯Cl1iii 0.94 (2) 2.25 (2) 3.1841 (13) 173 (2)
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Symmetry codes: (i) Inline graphic; (ii) Inline graphic; (iii) Inline graphic.

Figure 3.

Figure 3

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A fragment of the crystal packing of I.

Database survey  

A search of the Cambridge Structural Database (CSD, Version 5.36, last update May 2015; Groom & Allen, 2014 ▸) revealed that structures of phospho­nium salts having different alk­yl/ar­yl/biaryl substituents on phospho­rous are rare [CSD refcodes: BZMNPB (Böhme et al., 1975 ▸), EDOSOF (Schiemenz et al., 2002 ▸), SUXFUN (Dziuba et al., 2010 ▸)]. To the best of our knowledge I is the first example of a crystallographically characterized phospho­nium salt having four different substituents at phospho­rous. Moreover, there are only three other examples of structures of protonated phospho­nium ar­yl/biaryl salts [CSD refcodes: WEMSIQ (Carre et al., 1997 ▸), OCOWUY (Karaçar et al., 2001 ▸), TOMZIF (Wang et al., 2008 ▸)].

Synthesis and crystallization  

(2-{2,6-(OMe)2-Ph}-6-Me-Ph)(2-OMe-Ph)PCl (3) was synthesized by a modification of a previously reported procedure (Neuwald et al., 2013 ▸). The reaction of 3 with in situ-generated dili­thia­ted benzene­sulfonate was attempted to synthesize 2′ (see Scheme). However 31P and ESI–MS of the reaction mixture showed that 2′ was not formed. The reaction mixture was acidified with aqueous HCl and extracted with Et2O. After removal of volatiles from the Et2O fraction under vacuum, a yellow oil and white crystals (low yield) were obtained. Recrystallization of the white crystals from wet CH2Cl2/Et2O yielded crystals of [(2-{2,6-(OMe)2-Ph}-6-Me-Ph)(2-OMe-Ph)(n-Bu)PH]Cl·H2O (1·H2O, I), which was identified by X-ray crystallography analysis.

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. Most of the carbon-bound H atoms were included in idealized positions for structure factor calculations [C—H = 0.95–0.98 Å, U iso(H) set to 1.2–1.5U eq(C)]. The P—H hydrogen atom and the H atoms of the butyl group were located in a difference Fourier map and refined without additional restraints. The H atoms bound to oxygen atom O4 were also located in the difference Fourier map but were restrained to be at 0.96 Å from O4 (within 0.02 Å) with their thermal parameters set to 1.5U eq of O4.

Table 2. Experimental details.

Crystal data
Chemical formula C26H32O3P+·Cl−·H2O
M r 476.95
Crystal system, space group Triclinic, P Inline graphic
Temperature (K) 100
a, b, c (Å) 9.6920 (6), 10.2790 (6), 12.4154 (8)
α, β, γ (°) 96.836 (2), 98.481 (2), 94.188 (2)
V (Å3) 1209.47 (13)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.25
Crystal size (mm) 0.22 × 0.15 × 0.14
 
Data collection
Diffractometer Bruker D8 Venture PHOTON 100 CMOS
Absorption correction Numerical (SADABS; Bruker, 2014 ▸)
T min, T max 0.959, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections 33225, 6228, 5241
R int 0.028
(sin θ/λ)max (Å−1) 0.677
 
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S 0.038, 0.096, 1.04
No. of reflections 6228
No. of parameters 339
No. of restraints 2
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.51, −0.18
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Computer programs: APEX2 and SAINT (Bruker, 2012), SHELXT2014 (Sheldrick, 2015a ▸), SHELXL2014 (Sheldrick, 2015b ▸), OLEX2 (Dolomanov et al., 2009 ▸), Mercury (Macrae et al., 2008 ▸), and publCIF (Westrip, 2010 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015024780/hg5467sup1.cif

e-72-00174-sup1.cif (972.8KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015024780/hg5467Isup2.hkl

e-72-00174-Isup2.hkl (495KB, hkl)
Click here for additional data file. (4.5KB, cdx)

Supporting information file. DOI: 10.1107/S2056989015024780/hg5467Isup3.cdx

Click here for additional data file. (9.3KB, cml)

Supporting information file. DOI: 10.1107/S2056989015024780/hg5467Isup4.cml

CCDC reference: 1444199

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the National Science Foundation (grants CHE-0911180 and CHE-1048528).

supplementary crystallographic information

Crystal data

C26H32O3P+·Cl−·H2O Z = 2
Mr = 476.95 F(000) = 508
Triclinic, P1 Dx = 1.310 Mg m−3
a = 9.6920 (6) Å Mo Kα radiation, λ = 0.71073 Å
b = 10.2790 (6) Å Cell parameters from 9958 reflections
c = 12.4154 (8) Å θ = 2.4–28.7°
α = 96.836 (2)° µ = 0.25 mm−1
β = 98.481 (2)° T = 100 K
γ = 94.188 (2)° Block, colorless
V = 1209.47 (13) Å3 0.22 × 0.15 × 0.14 mm
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Data collection

Bruker D8 Venture PHOTON 100 CMOS diffractometer 6228 independent reflections
Radiation source: INCOATEC IµS micro-focus source 5241 reflections with I > 2σ(I)
Mirrors monochromator Rint = 0.028
Detector resolution: 10.4167 pixels mm-1 θmax = 28.8°, θmin = 2.1°
ω and phi scans h = −13→13
Absorption correction: numerical (SADABS; Bruker, 2014) k = −13→13
Tmin = 0.959, Tmax = 0.987 l = −16→16
33225 measured reflections
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Refinement

Refinement on F2 Primary atom site location: dual
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038 Hydrogen site location: mixed
wR(F2) = 0.096 H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0446P)2 + 0.6272P] where P = (Fo2 + 2Fc2)/3
6228 reflections (Δ/σ)max < 0.001
339 parameters Δρmax = 0.51 e Å−3
2 restraints Δρmin = −0.18 e Å−3
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Special details

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

x y z Uiso*/Ueq
Cl1 0.99543 (4) 0.06475 (3) 0.71011 (3) 0.02320 (9)
P1 0.22865 (3) 0.81030 (3) 0.70834 (3) 0.01537 (9)
H1P 0.1976 (17) 0.9280 (16) 0.6876 (14) 0.021 (4)*
O1 0.28474 (11) 0.98104 (10) 0.90415 (8) 0.0218 (2)
O2 0.41677 (10) 0.67819 (10) 0.96813 (8) 0.0191 (2)
O3 0.39185 (11) 0.49203 (9) 0.60356 (8) 0.0202 (2)
C1 0.14332 (15) 0.69712 (15) 0.59177 (11) 0.0191 (3)
H1A 0.1528 (17) 0.6081 (17) 0.6062 (14) 0.021 (4)*
H1B 0.0437 (19) 0.7148 (17) 0.5838 (14) 0.025 (4)*
C2 0.20590 (15) 0.71909 (15) 0.48809 (11) 0.0200 (3)
H2A 0.3053 (18) 0.7053 (16) 0.4998 (14) 0.020 (4)*
H2B 0.1977 (17) 0.8097 (17) 0.4745 (14) 0.021 (4)*
C3 0.13321 (16) 0.62469 (15) 0.38878 (12) 0.0228 (3)
H3A 0.035 (2) 0.6419 (17) 0.3743 (15) 0.028 (5)*
H3B 0.1359 (19) 0.5340 (19) 0.4054 (15) 0.029 (5)*
C4 0.20372 (19) 0.63906 (17) 0.28846 (13) 0.0266 (3)
H4A 0.300 (2) 0.6220 (18) 0.3021 (15) 0.027 (5)*
H4B 0.157 (2) 0.581 (2) 0.2247 (17) 0.038 (5)*
H4C 0.201 (2) 0.725 (2) 0.2709 (16) 0.034 (5)*
C5 0.15371 (14) 0.78501 (14) 0.82781 (11) 0.0165 (3)
C6 0.05961 (14) 0.67784 (15) 0.83277 (12) 0.0201 (3)
H6 0.0367 0.6102 0.7721 0.024*
C7 −0.00070 (15) 0.67025 (16) 0.92696 (13) 0.0239 (3)
H7 −0.0642 0.5969 0.9314 0.029*
C8 0.03227 (15) 0.77041 (16) 1.01452 (12) 0.0245 (3)
H8 −0.0104 0.7652 1.0782 0.029*
C9 0.12588 (15) 0.87774 (15) 1.01127 (12) 0.0225 (3)
H9 0.1471 0.9456 1.0718 0.027*
C10 0.18838 (14) 0.88450 (14) 0.91790 (11) 0.0186 (3)
C11 0.32790 (17) 1.08374 (15) 0.99388 (13) 0.0269 (3)
H11A 0.2459 1.1266 1.0125 0.040*
H11B 0.3947 1.1486 0.9728 0.040*
H11C 0.3727 1.0463 1.0577 0.040*
C12 0.43520 (17) 1.03920 (15) 0.66031 (14) 0.0288 (3)
H12A 0.5106 1.1035 0.6504 0.043*
H12B 0.3830 1.0780 0.7160 0.043*
H12C 0.3718 1.0145 0.5905 0.043*
C13 0.49738 (14) 0.91817 (13) 0.69739 (11) 0.0173 (3)
C14 0.41672 (13) 0.81018 (13) 0.72460 (10) 0.0141 (2)
C15 0.48062 (13) 0.70142 (12) 0.76063 (10) 0.0138 (2)
C16 0.62572 (14) 0.70164 (13) 0.76972 (11) 0.0165 (3)
H16 0.6703 0.6293 0.7952 0.020*
C17 0.70582 (14) 0.80644 (14) 0.74193 (11) 0.0185 (3)
H17 0.8045 0.8052 0.7476 0.022*
C18 0.64171 (15) 0.91265 (14) 0.70595 (11) 0.0192 (3)
H18 0.6974 0.9836 0.6866 0.023*
C19 0.39855 (13) 0.58266 (13) 0.78584 (11) 0.0145 (3)
C20 0.35655 (14) 0.47546 (13) 0.70350 (11) 0.0166 (3)
C21 0.28231 (14) 0.36210 (13) 0.72404 (12) 0.0197 (3)
H21 0.2515 0.2913 0.6671 0.024*
C22 0.25470 (14) 0.35547 (14) 0.82964 (13) 0.0212 (3)
H22 0.2044 0.2786 0.8446 0.025*
C23 0.29803 (14) 0.45739 (14) 0.91409 (12) 0.0202 (3)
H23 0.2791 0.4499 0.9861 0.024*
C24 0.36994 (14) 0.57144 (13) 0.89184 (11) 0.0164 (3)
C25 0.38278 (16) 0.67481 (16) 1.07612 (12) 0.0233 (3)
H25A 0.2811 0.6580 1.0716 0.035*
H25B 0.4148 0.7595 1.1211 0.035*
H25C 0.4291 0.6046 1.1097 0.035*
C26 0.36073 (17) 0.38149 (15) 0.51867 (12) 0.0267 (3)
H26A 0.4082 0.3066 0.5429 0.040*
H26B 0.3934 0.4048 0.4518 0.040*
H26C 0.2593 0.3577 0.5034 0.040*
O4 0.12871 (13) 0.13559 (12) 0.50244 (11) 0.0373 (3)
H4X 0.097 (2) 0.072 (2) 0.4420 (16) 0.056*
H4Y 0.085 (2) 0.108 (2) 0.5594 (16) 0.056*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Cl1 0.02306 (18) 0.02389 (18) 0.02263 (18) 0.00422 (13) 0.00472 (13) 0.00038 (13)
P1 0.01430 (16) 0.01926 (17) 0.01294 (17) 0.00220 (13) 0.00277 (12) 0.00249 (13)
O1 0.0250 (5) 0.0225 (5) 0.0166 (5) −0.0003 (4) 0.0035 (4) −0.0008 (4)
O2 0.0213 (5) 0.0242 (5) 0.0124 (5) 0.0012 (4) 0.0050 (4) 0.0025 (4)
O3 0.0268 (5) 0.0180 (5) 0.0148 (5) −0.0052 (4) 0.0061 (4) −0.0008 (4)
C1 0.0161 (6) 0.0259 (7) 0.0145 (6) 0.0002 (5) 0.0012 (5) 0.0024 (5)
C2 0.0201 (7) 0.0246 (7) 0.0150 (7) 0.0006 (6) 0.0029 (5) 0.0020 (5)
C3 0.0250 (8) 0.0263 (8) 0.0167 (7) 0.0005 (6) 0.0029 (6) 0.0021 (6)
C4 0.0359 (9) 0.0280 (8) 0.0164 (7) 0.0028 (7) 0.0079 (6) 0.0002 (6)
C5 0.0138 (6) 0.0232 (7) 0.0138 (6) 0.0049 (5) 0.0038 (5) 0.0038 (5)
C6 0.0148 (6) 0.0265 (7) 0.0192 (7) 0.0026 (5) 0.0027 (5) 0.0034 (6)
C7 0.0148 (6) 0.0341 (8) 0.0250 (8) 0.0013 (6) 0.0059 (5) 0.0094 (6)
C8 0.0177 (7) 0.0401 (9) 0.0192 (7) 0.0092 (6) 0.0076 (5) 0.0086 (6)
C9 0.0211 (7) 0.0301 (8) 0.0172 (7) 0.0100 (6) 0.0041 (5) 0.0013 (6)
C10 0.0169 (6) 0.0223 (7) 0.0172 (7) 0.0058 (5) 0.0015 (5) 0.0042 (5)
C11 0.0322 (8) 0.0238 (7) 0.0219 (7) 0.0016 (6) 0.0004 (6) −0.0036 (6)
C12 0.0285 (8) 0.0207 (7) 0.0391 (9) 0.0007 (6) 0.0052 (7) 0.0133 (7)
C13 0.0210 (7) 0.0156 (6) 0.0151 (6) −0.0004 (5) 0.0032 (5) 0.0018 (5)
C14 0.0137 (6) 0.0167 (6) 0.0118 (6) −0.0001 (5) 0.0030 (5) 0.0006 (5)
C15 0.0155 (6) 0.0155 (6) 0.0098 (6) −0.0016 (5) 0.0031 (5) 0.0001 (5)
C16 0.0161 (6) 0.0180 (6) 0.0155 (6) 0.0026 (5) 0.0032 (5) 0.0013 (5)
C17 0.0151 (6) 0.0222 (7) 0.0176 (7) −0.0010 (5) 0.0048 (5) −0.0009 (5)
C18 0.0204 (7) 0.0184 (6) 0.0182 (7) −0.0058 (5) 0.0058 (5) 0.0012 (5)
C19 0.0123 (6) 0.0161 (6) 0.0159 (6) 0.0013 (5) 0.0024 (5) 0.0047 (5)
C20 0.0146 (6) 0.0181 (6) 0.0173 (6) 0.0011 (5) 0.0026 (5) 0.0041 (5)
C21 0.0168 (6) 0.0163 (6) 0.0257 (7) −0.0007 (5) 0.0021 (5) 0.0045 (5)
C22 0.0154 (6) 0.0210 (7) 0.0296 (8) −0.0004 (5) 0.0056 (5) 0.0113 (6)
C23 0.0166 (6) 0.0268 (7) 0.0208 (7) 0.0035 (5) 0.0071 (5) 0.0114 (6)
C24 0.0134 (6) 0.0200 (6) 0.0171 (6) 0.0041 (5) 0.0035 (5) 0.0050 (5)
C25 0.0236 (7) 0.0348 (8) 0.0147 (7) 0.0091 (6) 0.0079 (5) 0.0059 (6)
C26 0.0329 (8) 0.0233 (7) 0.0209 (7) −0.0081 (6) 0.0074 (6) −0.0062 (6)
O4 0.0384 (7) 0.0375 (7) 0.0322 (7) −0.0162 (5) 0.0104 (5) −0.0042 (5)
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Geometric parameters (Å, º)

P1—C5 1.7824 (14) C11—H11B 0.9800
P1—C1 1.7994 (14) C11—H11C 0.9800
P1—C14 1.8043 (13) C12—C13 1.512 (2)
P1—H1P 1.313 (16) C12—H12A 0.9800
O1—C10 1.3557 (17) C12—H12B 0.9800
O1—C11 1.4313 (17) C12—H12C 0.9800
O2—C24 1.3639 (17) C13—C18 1.3930 (19)
O2—C25 1.4307 (16) C13—C14 1.4135 (18)
O3—C20 1.3611 (16) C14—C15 1.4042 (18)
O3—C26 1.4367 (17) C15—C16 1.3940 (18)
C1—C2 1.5347 (19) C15—C19 1.4979 (17)
C1—H1A 0.962 (17) C16—C17 1.3884 (19)
C1—H1B 0.988 (18) C16—H16 0.9500
C2—C3 1.522 (2) C17—C18 1.382 (2)
C2—H2A 0.976 (17) C17—H17 0.9500
C2—H2B 0.973 (17) C18—H18 0.9500
C3—C4 1.523 (2) C19—C24 1.4005 (18)
C3—H3A 0.975 (19) C19—C20 1.4030 (18)
C3—H3B 0.980 (19) C20—C21 1.3939 (19)
C4—H4A 0.952 (19) C21—C22 1.385 (2)
C4—H4B 0.96 (2) C21—H21 0.9500
C4—H4C 0.94 (2) C22—C23 1.385 (2)
C5—C6 1.391 (2) C22—H22 0.9500
C5—C10 1.4058 (19) C23—C24 1.3967 (19)
C6—C7 1.390 (2) C23—H23 0.9500
C6—H6 0.9500 C25—H25A 0.9800
C7—C8 1.388 (2) C25—H25B 0.9800
C7—H7 0.9500 C25—H25C 0.9800
C8—C9 1.385 (2) C26—H26A 0.9800
C8—H8 0.9500 C26—H26B 0.9800
C9—C10 1.3913 (19) C26—H26C 0.9800
C9—H9 0.9500 O4—H4X 0.933 (16)
C11—H11A 0.9800 O4—H4Y 0.935 (16)
C5—P1—C1 110.72 (7) H11B—C11—H11C 109.5
C5—P1—C14 115.02 (6) C13—C12—H12A 109.5
C1—P1—C14 111.73 (6) C13—C12—H12B 109.5
C5—P1—H1P 104.9 (7) H12A—C12—H12B 109.5
C1—P1—H1P 106.2 (7) C13—C12—H12C 109.5
C14—P1—H1P 107.5 (7) H12A—C12—H12C 109.5
C10—O1—C11 117.40 (11) H12B—C12—H12C 109.5
C24—O2—C25 117.30 (11) C18—C13—C14 118.04 (12)
C20—O3—C26 117.23 (11) C18—C13—C12 118.55 (12)
C2—C1—P1 111.17 (10) C14—C13—C12 123.41 (12)
C2—C1—H1A 109.2 (10) C15—C14—C13 120.89 (12)
P1—C1—H1A 110.0 (10) C15—C14—P1 119.76 (10)
C2—C1—H1B 111.4 (10) C13—C14—P1 119.31 (10)
P1—C1—H1B 105.0 (10) C16—C15—C14 118.88 (12)
H1A—C1—H1B 110.1 (14) C16—C15—C19 118.49 (12)
C3—C2—C1 111.50 (12) C14—C15—C19 122.59 (11)
C3—C2—H2A 108.6 (10) C17—C16—C15 120.72 (13)
C1—C2—H2A 109.4 (10) C17—C16—H16 119.6
C3—C2—H2B 110.2 (10) C15—C16—H16 119.6
C1—C2—H2B 109.0 (10) C18—C17—C16 119.89 (13)
H2A—C2—H2B 108.0 (14) C18—C17—H17 120.1
C2—C3—C4 111.23 (12) C16—C17—H17 120.1
C2—C3—H3A 108.7 (11) C17—C18—C13 121.55 (12)
C4—C3—H3A 110.7 (11) C17—C18—H18 119.2
C2—C3—H3B 109.5 (11) C13—C18—H18 119.2
C4—C3—H3B 109.1 (11) C24—C19—C20 118.43 (12)
H3A—C3—H3B 107.5 (15) C24—C19—C15 121.77 (12)
C3—C4—H4A 111.1 (11) C20—C19—C15 119.66 (11)
C3—C4—H4B 111.9 (12) O3—C20—C21 123.42 (12)
H4A—C4—H4B 108.7 (16) O3—C20—C19 115.07 (11)
C3—C4—H4C 110.1 (12) C21—C20—C19 121.51 (13)
H4A—C4—H4C 107.5 (16) C22—C21—C20 118.23 (13)
H4B—C4—H4C 107.3 (16) C22—C21—H21 120.9
C6—C5—C10 120.16 (12) C20—C21—H21 120.9
C6—C5—P1 123.45 (11) C21—C22—C23 122.09 (13)
C10—C5—P1 116.29 (10) C21—C22—H22 119.0
C7—C6—C5 119.61 (13) C23—C22—H22 119.0
C7—C6—H6 120.2 C22—C23—C24 119.05 (13)
C5—C6—H6 120.2 C22—C23—H23 120.5
C8—C7—C6 119.68 (14) C24—C23—H23 120.5
C8—C7—H7 120.2 O2—C24—C23 124.22 (12)
C6—C7—H7 120.2 O2—C24—C19 115.16 (12)
C9—C8—C7 121.58 (13) C23—C24—C19 120.62 (13)
C9—C8—H8 119.2 O2—C25—H25A 109.5
C7—C8—H8 119.2 O2—C25—H25B 109.5
C8—C9—C10 118.89 (14) H25A—C25—H25B 109.5
C8—C9—H9 120.6 O2—C25—H25C 109.5
C10—C9—H9 120.6 H25A—C25—H25C 109.5
O1—C10—C9 125.57 (13) H25B—C25—H25C 109.5
O1—C10—C5 114.38 (12) O3—C26—H26A 109.5
C9—C10—C5 120.05 (13) O3—C26—H26B 109.5
O1—C11—H11A 109.5 H26A—C26—H26B 109.5
O1—C11—H11B 109.5 O3—C26—H26C 109.5
H11A—C11—H11B 109.5 H26A—C26—H26C 109.5
O1—C11—H11C 109.5 H26B—C26—H26C 109.5
H11A—C11—H11C 109.5 H4X—O4—H4Y 105 (2)
C5—P1—C1—C2 179.34 (10) C13—C14—C15—C19 −177.42 (12)
C14—P1—C1—C2 −51.05 (12) P1—C14—C15—C19 0.53 (17)
P1—C1—C2—C3 −179.38 (10) C14—C15—C16—C17 −1.07 (19)
C1—C2—C3—C4 −175.19 (13) C19—C15—C16—C17 176.72 (12)
C1—P1—C5—C6 10.21 (14) C15—C16—C17—C18 0.7 (2)
C14—P1—C5—C6 −117.62 (12) C16—C17—C18—C13 0.5 (2)
C1—P1—C5—C10 −166.26 (10) C14—C13—C18—C17 −1.2 (2)
C14—P1—C5—C10 65.91 (12) C12—C13—C18—C17 178.38 (13)
C10—C5—C6—C7 0.5 (2) C16—C15—C19—C24 90.26 (16)
P1—C5—C6—C7 −175.84 (11) C14—C15—C19—C24 −92.04 (16)
C5—C6—C7—C8 0.8 (2) C16—C15—C19—C20 −85.45 (16)
C6—C7—C8—C9 −0.9 (2) C14—C15—C19—C20 92.25 (16)
C7—C8—C9—C10 −0.2 (2) C26—O3—C20—C21 −5.6 (2)
C11—O1—C10—C9 1.2 (2) C26—O3—C20—C19 175.38 (12)
C11—O1—C10—C5 −178.31 (12) C24—C19—C20—O3 −178.00 (11)
C8—C9—C10—O1 −177.92 (13) C15—C19—C20—O3 −2.15 (18)
C8—C9—C10—C5 1.5 (2) C24—C19—C20—C21 2.9 (2)
C6—C5—C10—O1 177.84 (12) C15—C19—C20—C21 178.79 (12)
P1—C5—C10—O1 −5.57 (16) O3—C20—C21—C22 178.79 (12)
C6—C5—C10—C9 −1.7 (2) C19—C20—C21—C22 −2.2 (2)
P1—C5—C10—C9 174.93 (10) C20—C21—C22—C23 0.2 (2)
C18—C13—C14—C15 0.86 (19) C21—C22—C23—C24 1.0 (2)
C12—C13—C14—C15 −178.75 (13) C25—O2—C24—C23 −3.54 (19)
C18—C13—C14—P1 −177.10 (10) C25—O2—C24—C19 176.32 (11)
C12—C13—C14—P1 3.30 (18) C22—C23—C24—O2 179.57 (12)
C5—P1—C14—C15 55.82 (12) C22—C23—C24—C19 −0.3 (2)
C1—P1—C14—C15 −71.50 (12) C20—C19—C24—O2 178.49 (11)
C5—P1—C14—C13 −126.20 (11) C15—C19—C24—O2 2.72 (18)
C1—P1—C14—C13 106.48 (11) C20—C19—C24—C23 −1.65 (19)
C13—C14—C15—C16 0.27 (19) C15—C19—C24—C23 −177.41 (12)
P1—C14—C15—C16 178.22 (10)
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Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A
P1—H1P···Cl1i 1.313 (16) 2.523 (16) 3.5798 (5) 135.5 (10)
C21—H21···O4 0.95 2.53 3.4594 (19) 167
C26—H26C···O4 0.98 2.53 3.2250 (19) 128
O4—H4X···Cl1ii 0.93 (2) 2.24 (2) 3.1717 (13) 173 (2)
O4—H4Y···Cl1iii 0.94 (2) 2.25 (2) 3.1841 (13) 173 (2)
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Symmetry codes: (i) x−1, y+1, z; (ii) −x+1, −y, −z+1; (iii) x−1, y, z.

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015024780/hg5467sup1.cif

e-72-00174-sup1.cif (972.8KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015024780/hg5467Isup2.hkl

e-72-00174-Isup2.hkl (495KB, hkl)
Click here for additional data file. (4.5KB, cdx)

Supporting information file. DOI: 10.1107/S2056989015024780/hg5467Isup3.cdx

Click here for additional data file. (9.3KB, cml)

Supporting information file. DOI: 10.1107/S2056989015024780/hg5467Isup4.cml

CCDC reference: 1444199

Additional supporting information: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography

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