2-[anilino(diphenylphosphoryl)methyl]phenol from a three-component Kabachnik-Fields reaction

Article abstract of DOI:10.1107/S0108270113022087

The title compound, C₂₅H₂₂NO₂P, was synthesized in high yield by a three-component Kabachnik-Fields reaction of diphenylphosphine oxide, salicylaldehyde and aniline in dry toluene at room temperature. It precipitates as racemic crystals, in which strong hydrogen bonds between the hydroxy group and the P=O group of a neighbouring molecule form one-dimensional heterochiral chains along the crystallographic a axis, with an O...O separation of 2.568 (2) A. The pseudo-tetrahedral environment of the P atom is distorted, with O - P - C bond angles significantly larger than the C - P - C angles.

Full text of DOI:10.1107/S0108270113022087

organic compounds
Acta Crystallographica Section C
Crystal Structure
Communications
synthetic access. We report herein a convenient one-pot three-
component method using a Kabachnik–Fields reaction for
the synthesis of 2-[anilino(diphenylphosphoryl)methyl]phenol,
(I), using diphenylphosphine oxide, salicylaldehyde and aniline
as starting materials (see Scheme). The notable advantages of
this methodology are operational simplicity, mild reaction
conditions, higher yields, a reasonable reaction time and ease
of isolation of the pure products. In order to confirm further
the stereochemistry and structure–activity relationship of
ꢀ-aminophosphine oxides with potential practical applica-
tions, we established the crystal structure of (I).
ISSN 0108-2701
2-[Anilino(diphenylphosphoryl)-
methyl]phenol from a three-
component Kabachnik–Fields
reaction
Ming-Shu Wu,a* Qing-Qin Feng,b Gao-Nan Lia and
De-Hui Wana
aCollege of Chemistry and Chemical Engineering, Hainan Normal University, Haikou
571158, People’s Republic of China, and bCollege of Chemistry and Chemical
Engineering, Anyang Normal University, Anyang, Henan 455000, People’s Republic
of China
Correspondence e-mail: wumingshu@126.com
Received 3 July 2013
Accepted 7 August 2013
The title compound, C25H22NO2P, was synthesized in high
yield by a three-component Kabachnik–Fields reaction of
diphenylphosphine oxide, salicylaldehyde and aniline in dry
toluene at room temperature. It precipitates as racemic
crystals, in which strong hydrogen bonds between the hydroxy
group and the P O group of a neighbouring molecule form
one-dimensional heterochiral chains along the crystallo-
2. Experimental
2.1. Synthesis and crystallization
A solution of diphenylphosphine oxide (1.01 g, 5 mmol,
1 equivalent) in dry toluene (10 ml) was added to a dry 50 ml
flask (equipped with a CaCl2 tube) containing a solution of
aniline (1.8 ml, 20 mmol, 4 equivalents) and salicylaldehyde
(0.61 g, 5 mmol, 1 equivalent) in dry toluene (20 ml). After
stirring for 4 h at room temperature, the reaction was
complete; the precipitate was filtered off, washed with cold
toluene (10 ml) and then dried under vacuum to afford the
pure title product, (I) (yield 1.8 g, 90%), as a colourless solid.
Single crystals of (I) suitable for X-ray diffraction were
obtained by recrystallization from diethyl ether. Spectroscopic
˚
graphic a axis, with an Oꢀ ꢀ ꢀO separation of 2.568 (2) A. The
pseudo-tetrahedral environment of the P atom is distorted,
with O—P—C bond angles significantly larger than the C—
P—C angles.
Keywords: crystal structure; Kabachnik–Fields reaction;
heterochiral chains.
1. Introduction
1
analysis: H NMR (400 MHz, CDCl3, 298 K): ꢁ 9.82 (s, 1H,
Chiral phosphorus-containing compounds such as ꢀ-amino-
phosphonic acids and their derivatives have attracted
considerable attention due to their promising biological
properties (Romanenko & Kukhar, 2006; Haynes et al., 1989,
1991; Shi et al., 2000; Kafarski & Lejczak, 2001). They have
found application as antibacterials (Pratt, 1989), antiviral
agents (Huang & Chen, 2000) and enzyme inhibitors (Smith et
al., 1989; Kafarski & Lejczak, 1991). The absolute configura-
tion of phosphonyl compounds strongly influences their
biological properties (Patel et al., 1995). Various methods for
the synthesis of ꢀ-aminophosphonic acids and ꢀ-amino-
phosphonates have therefore been reported (Moore et al.,
2
OH), 7.81–6.62 (m, 19H, Ar-H), 5.46 (d, JP—H = 8.5 Hz, 1H,
C—H), 3.73 (br s, 1H, NH); 13C NMR (100 MHz, CDCl3,
298 K): ꢁ 155.9, 145.8, 132.7, 129.3, 129.7, 129.2, 128.8, 128.6,
128.4, 128.3, 122.4, 120.4, 119.2, 114.4, 56.9 (d, JP—C
1
=
39.9 Hz); 31P NMR (162 MHz, CDCl3, 298 K): ꢁ 38.4; IR (KBr,
ꢂ, cmꢁ1): 3430 (NH), 3228 (OH), 3303 (NH), 3138, 3062, 2969,
2916, 2884, 2827, 1591, 1553, 1485, 1438, 1171 (P O), 1122,
1096 (P—O), 1070, 1037, 855, 743, 726, 693, 561, 542, 525, 439.
Analysis found for C25H22NO2P: C 75.19, H 5.43, N 3.55%;
calculated: C 75.18, H 5.55, N 3.51%.
2.2. Refinement
´
2002; Demmer et al., 2011; Balint et al., 2013; Wu et al., 2013).
However, other ꢀ-amino phosphorus derivatives, such as
ꢀ-aminophosphine oxides, have received much less attention
for their biological properties due to the lack of direct
Crystal data, data collection and structure refinement
details are summarized in Table 1. H atoms bound to C or N
atoms were positioned geometrically and refined using a
1070 # 2013 International Union of Crystallography
doi:10.1107/S0108270113022087
Acta Cryst. (2013). C69, 1070–1072

organic compounds
Table 1
Experimental details.
Crystal data
Chemical formula
Mr
C25H22NO2P
399.41
Crystal system, space group
Temperature (K)
Orthorhombic, Pbca
293
12.5489 (4), 16.4560 (5), 20.9643 (6)
4329.2 (2)
8
Mo Kꢀ
0.15
0.1 ꢃ 0.1 ꢃ 0.1
˚
a, b, c (A)
3
˚
V (A )
Z
Radiation type
ꢃ (mmꢁ1
Crystal size (mm)
)
Data collection
Diffractometer
Agilent Xcalibur (Atlas, Gemini
ultra) diffractometer
Multi-scan (CrysAlis PRO; Agilent,
2012)
Absorption correction
Tmin, Tmax
0.774, 1.000
14390, 4429, 2951
No. of measured, independent and
observed [I > 2ꢄ(I)] reflections
Rint
0.039
0.625
ꢁ1
˚
(sin ꢅ/ꢆ)max (A
)
Refinement
R[F2 > 2ꢄ(F2)], wR(F2), S
No. of reflections
0.048, 0.122, 1.02
4429
263
0
H-atom parameters constrained
No. of parameters
No. of restraints
H-atom treatment
ꢁ3
˚
Figure 2
Packing for (I), showing the intermolecular hydrogen-bonding inter-
Áꢇmax, Áꢇmin (e A
)
0.29, ꢁ0.27
Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008),
SHELXL97 (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009).
actions (dashed lines) between atoms H1B and O2i of neighbouring S and
1
3
R enantiomers. [Symmetry code: (i) x ꢁ , y, ꢁz + .]
2
2
˚
riding model, with aryl C—H = 0.93 A, methine C—H =
3. Results and discussion
˚
˚
0.98 A and N—H = 0.86 A, and with Uiso(H) = 1.2Ueq(C,N).
The hydroxy H atom was located from a difference Fourier
map and was refined with a combination of riding and rota-
tional motion, with Uiso(H) = 1.5Ueq(O).
In compound (I), the formation of P—C bonds between the P
atom of diphenylphosphine oxide and the carbonyl C atom of
salicylaldehyde generates a stereocentre at atom C7 (Fig. 1).
The space group Pbca was identified with the help of the
program PLATON (Spek, 2009). Not surprisingly, (I) forms
racemic crystals with one molecule in the asymmetric unit. A
displacement ellipsoid plot of the S enantiomer is shown in
Fig. 1. The O—P—C bond angles are systematically larger
than the C—P—C angles (Table 2), indicating a minor
distortion in which the phenyl groups are splayed back slightly,
away from the phosphoryl function.
An intermolecular O1—H1ꢀ ꢀ ꢀO2i hydrogen bond (details
in Table 3, including symmetry code) between the O1—H1
hydroxy group and P-bonded atom O2 links neighbouring
Table 2
Selected bond angles (ꢄ).
O2—P1—C7
O2—P1—C19
O2—P1—C25
110.33 (9)
110.55 (9)
114.61 (9)
C19—P1—C7
C25—P1—C7
C25—P1—C19
108.59 (9)
105.28 (9)
107.19 (9)
Table 3
Hydrogen-bond geometry (A, ).
ꢄ
˚
D—Hꢀ ꢀ ꢀA
O1—H1Bꢀ ꢀ ꢀO2i
Symmetry code: (i) x ꢁ ; y; ꢁz þ .
D—H
Hꢀ ꢀ ꢀA
Dꢀ ꢀ ꢀA
D—Hꢀ ꢀ ꢀA
Figure 1
The molecular structure of (I), showing the atom-labelling scheme.
Displacement ellipsoids are drawn at the 50% probability level.
0.82
1.79
2.5677 (19)
159
1
2
3
2
ꢂ
Acta Cryst. (2013). C69, 1070–1072
Wu et al. C25H22NO2P 1071

organic compounds
Haynes, R. K., Loughlin, W. A. & Hambley, T. W. (1991). J. Org. Chem. 56,
5785–5790.
Haynes, R. K., Vonwiller, S. C. & Hambley, T. W. (1989). J. Org. Chem. 54,
5162–5170.
molecules into heterochiral chains along the crystallographic a
axis (Fig. 2).
Huang, J. & Chen, R. (2000). Heteroatom Chem. 11, 480–492.
Kafarski, P. & Lejczak, B. (1991). Phosphorus Sulfur Silicon Relat. Elem. 63,
193–215.
This work was supported by the National Natural Science
Foundation of China (grant No. 21162008).
Kafarski, P. & Lejczak, B. (2001). Curr. Med. Chem. 1, 301–312.
Moore, J. D., Sprott, K. T. & Hanson, P. R. (2002). J. Org. Chem. 67, 8123–
8129.
Patel, D. V., Rielly-Gauvin, K., Ryono, D. E., Charles, A. F., Rogers, W. L.,
Smith, S. A., Deforrest, J. M., Oehl, R. S. & Petrillo, E. W. (1995). J. Med.
Chem. 38, 4557–4569.
Supplementary data for this paper are available from the IUCr electronic
archives (Reference: EG3131). Services for accessing these data are
described at the back of the journal.
Pratt, R. F. (1989). Science, 246, 917–919.
References
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Shi, J.-C., Chao, H.-Y., Fu, W.-F., Peng, S.-M. & Che, C.-M. (2000). J. Chem.
Soc. Dalton Trans. 18, 3128–3132.
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire,
England.
´ ´
Balint, E., Takacs, J., Drahos, L. & Juranovic, A. (2013). Heteroatom Chem. 24,
221–225.
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7981–8006.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann,
H. (2009). J. Appl. Cryst. 42, 339–341.
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12819.
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ꢂ
1072 Wu et al. C25H22NO2P
Acta Cryst. (2013). C69, 1070–1072

supplementary materials
supplementary materials
Acta Cryst. (2013). C69, 1070-1072 [doi:10.1107/S0108270113022087]
2-[Anilino(diphenylphosphoryl)methyl]phenol from a three-component
Kabachnik–Fields reaction
Ming-Shu Wu, Qing-Qin Feng, Gao-Nan Li and De-Hui Wan
Computing details
Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis
PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine
structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare
material for publication: OLEX2 (Dolomanov et al., 2009).
2-[Anilino(diphenylphosphoryl)methyl]phenol
Crystal data
C25H22NO2P
Mr = 399.41
Dx = 1.226 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 3813 reflections
θ = 2.3–29.7°
Orthorhombic, Pbca
a = 12.5489 (4) Å
b = 16.4560 (5) Å
c = 20.9643 (6) Å
V = 4329.2 (2) Å3
Z = 8
µ = 0.15 mm−1
T = 293 K
Prism, colourless
0.1 × 0.1 × 0.1 mm
F(000) = 1680
Data collection
Agilent Xcalibur (Atlas, Gemini ultra)
diffractometer
Radiation source: fine-focus sealed tube
Graphite monochromator
ω scans
14390 measured reflections
4429 independent reflections
2951 reflections with I > 2σ(I)
Rint = 0.039
θ
max = 26.4°, θmin = 2.3°
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2012)
h = −14→15
k = −20→16
l = −26→25
T
min = 0.774, Tmax = 1.000
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.048
wR(F2) = 0.122
Secondary atom site location: difference Fourier
map
Hydrogen site location: inferred from
neighbouring sites
S = 1.02
4429 reflections
263 parameters
0 restraints
Primary atom site location: structure-invariant
direct methods
H-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0503P)2 + 0.6207P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.29 e Å−3
Δρmin = −0.27 e Å−3
Acta Cryst. (2013). C69, 1070-1072
sup-1

supplementary materials
Special details
Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16) Empirical absorption correction using spherical harmonics, implemented in SCALE3
ABSPACK scaling algorithm.
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)
x
y
z
Uiso*/Ueq
P1
0.68854 (4)
0.43871 (13)
0.3989
0.10727 (3)
0.17634 (11)
0.1774
0.67088 (2)
0.75461 (7)
0.7856
0.03680 (16)
0.0704 (5)
0.106*
O1
H1B
O2
0.79368 (10)
0.59018 (14)
0.6477
0.14729 (9)
0.21014 (10)
0.2017
0.66206 (6)
0.59205 (7)
0.5708
0.0484 (4)
0.0476 (4)
0.057*
N1
H1
C1
0.65930 (19)
0.7084
0.30369 (13)
0.3083
0.71138 (11)
0.6784
0.0559 (6)
0.067*
H1A
C2
0.6630 (2)
0.7144
0.35799 (15)
0.3987
0.76194 (13)
0.7629
0.0732 (7)
0.088*
H2
C3
0.5904 (2)
0.5931
0.35127 (16)
0.3876
0.81021 (12)
0.8442
0.0693 (7)
0.083*
H3
C4
0.5139 (2)
0.4646
0.29207 (15)
0.2885
0.80944 (10)
0.8424
0.0603 (6)
0.072*
H4
C5
0.51038 (17)
0.58356 (16)
0.58122 (15)
0.5136
0.23744 (13)
0.24296 (11)
0.17948 (12)
0.1500
0.75920 (9)
0.70957 (9)
0.65686 (8)
0.6602
0.0466 (5)
0.0392 (5)
0.0384 (5)
0.046*
C6
C7
H7
C8
0.41040 (18)
0.3999
0.26471 (13)
0.2444
0.59454 (10)
0.6355
0.0514 (6)
0.062*
H8
C9
0.3292 (2)
0.2646
0.30678 (15)
0.3146
0.56417 (12)
0.5850
0.0668 (7)
0.080*
H9
C10
H10
C11
H11
C12
H12
C13
C14
H14
C15
H15
C16
0.3430 (3)
0.2881
0.33700 (16)
0.3651
0.50364 (14)
0.4836
0.0758 (8)
0.091*
0.4382 (3)
0.4478
0.32536 (16)
0.3458
0.47317 (12)
0.4322
0.0740 (8)
0.089*
0.5201 (2)
0.5843
0.28378 (13)
0.2763
0.50237 (10)
0.4810
0.0561 (6)
0.067*
0.50706 (18)
0.5774 (2)
0.5149
0.25279 (11)
−0.00203 (15)
0.0253
0.56411 (9)
0.59125 (10)
0.6019
0.0433 (5)
0.0621 (6)
0.075*
0.5736 (3)
0.5086
−0.06854 (17)
−0.0861
0.55043 (12)
0.5342
0.0788 (8)
0.095*
0.6647 (3)
−0.10775 (17)
0.53429 (13)
0.0860 (10)
Acta Cryst. (2013). C69, 1070-1072
sup-2

supplementary materials
H16
C17
H17
C18
H18
C19
C20
H20
C21
H21
C22
H22
C23
H23
C24
H24
C25
0.6619
−0.1523
0.5071
0.103*
0.7601 (3)
0.8221
−0.08252 (17)
−0.1096
0.55751 (14)
0.5458
0.0857 (9)
0.103*
0.7655 (2)
0.8310
−0.01646 (14)
0.0006
0.59873 (11)
0.6145
0.0640 (7)
0.077*
0.67364 (17)
0.7151 (2)
0.7624
0.02364 (12)
0.10357 (17)
0.1463
0.61607 (9)
0.80119 (10)
0.7948
0.0428 (5)
0.0719 (8)
0.086*
0.6948 (3)
0.7280
0.0757 (2)
0.1003
0.86265 (12)
0.8973
0.0975 (11)
0.117*
0.6265 (3)
0.6143
0.0125 (2)
−0.0067
0.87217 (12)
0.9133
0.0874 (9)
0.105*
0.5764 (2)
0.5290
−0.02250 (17)
−0.0651
0.82197 (13)
0.8287
0.0783 (8)
0.094*
0.5956 (2)
0.5609
0.00505 (14)
−0.0193
0.76081 (10)
0.7266
0.0609 (6)
0.073*
0.66542 (16)
0.06800 (12)
0.74989 (9)
0.0426 (5)
Atomic displacement parameters (Å2)
U11
U22
U33
U12
U13
U23
P1
0.0374 (3)
0.0646 (11)
0.0378 (8)
0.0492 (11)
0.0629 (15)
0.0790 (19)
0.084 (2)
0.0433 (3)
0.0297 (3)
0.0609 (10)
0.0391 (7)
0.0333 (8)
0.0574 (14)
0.089 (2)
−0.0013 (2)
−0.0245 (10)
−0.0077 (7)
0.0079 (9)
−0.0015 (2)
0.0271 (8)
0.0009 (2)
O1
0.0858 (12)
0.0683 (9)
0.0603 (11)
0.0474 (13)
0.0521 (15)
0.0586 (16)
0.0659 (16)
0.0501 (12)
0.0384 (11)
0.0429 (11)
0.0535 (13)
0.0640 (16)
0.0604 (17)
0.0609 (16)
0.0524 (13)
0.0371 (11)
0.0622 (15)
0.0678 (17)
0.0524 (16)
0.0599 (17)
0.0570 (15)
0.0400 (11)
0.0932 (19)
0.128 (3)
−0.0124 (9)
−0.0007 (7)
0.0097 (8)
O2
−0.0011 (6)
0.0064 (8)
N1
C1
−0.0102 (12)
−0.0140 (14)
0.0075 (15)
0.0117 (14)
0.0012 (11)
0.0008 (9)
0.0067 (12)
−0.0039 (16)
−0.0063 (15)
0.0073 (12)
0.0035 (10)
0.0000 (9)
0.0012 (11)
−0.0097 (14)
−0.0203 (13)
−0.0074 (11)
0.0010 (10)
0.0045 (9)
C2
C3
0.0657 (16)
0.0479 (12)
0.0430 (11)
0.0370 (10)
0.0332 (10)
0.0436 (12)
0.0702 (16)
0.0743 (18)
0.0527 (14)
0.0400 (11)
0.0362 (10)
0.0539 (13)
0.0595 (16)
0.0574 (16)
0.081 (2)
C4
0.0673 (16)
0.0465 (12)
0.0421 (12)
0.0390 (11)
0.0570 (14)
0.0662 (17)
0.093 (2)
C5
C6
C7
−0.0034 (9)
0.0074 (11)
0.0141 (13)
0.0103 (15)
−0.0108 (16)
−0.0113 (12)
−0.0034 (10)
−0.0032 (13)
−0.0205 (18)
−0.006 (2)
0.0006 (8)
0.0051 (8)
C8
−0.0110 (11)
−0.0229 (13)
−0.0419 (17)
−0.0350 (16)
−0.0120 (11)
−0.0102 (10)
−0.0079 (13)
−0.0115 (16)
0.0084 (19)
0.0206 (19)
0.0016 (13)
−0.0007 (10)
−0.0057 (12)
−0.0097 (15)
0.0147 (17)
0.0200 (17)
0.0037 (12)
−0.0008 (9)
−0.0036 (10)
−0.0157 (13)
−0.0013 (14)
0.0141 (12)
0.0062 (10)
−0.0019 (9)
−0.0116 (12)
−0.0111 (14)
−0.0091 (13)
−0.0111 (15)
−0.0042 (12)
0.0016 (9)
C9
C10
C11
C12
C13
C14
C15
C16
C17
C18
C19
C20
C21
C22
C23
C24
C25
0.108 (2)
0.0759 (16)
0.0567 (14)
0.0703 (17)
0.109 (2)
0.148 (3)
0.116 (3)
0.0229 (18)
0.0125 (14)
0.0011 (10)
−0.0216 (16)
−0.021 (2)
0.0740 (18)
0.0567 (14)
0.0852 (19)
0.129 (3)
0.0609 (14)
0.0318 (10)
0.0372 (12)
0.0357 (14)
0.0450 (15)
0.0714 (18)
0.0491 (13)
0.0347 (10)
0.0073 (13)
0.0118 (16)
0.0264 (15)
0.0246 (14)
0.0112 (11)
0.0043 (9)
0.125 (3)
0.092 (2)
0.011 (2)
0.100 (2)
0.0636 (17)
0.0593 (15)
0.0456 (11)
−0.0068 (16)
−0.0074 (13)
0.0048 (10)
0.0745 (17)
0.0475 (12)
Acta Cryst. (2013). C69, 1070-1072
sup-3

supplementary materials
Geometric parameters (Å, º)
P1—O2
P1—C7
1.4862 (14)
1.820 (2)
1.803 (2)
1.8015 (19)
0.8200
C11—H11
C12—C11
C12—H12
C13—C8
0.9300
1.378 (3)
0.9300
P1—C19
P1—C25
O1—H1B
N1—H1
N1—C13
C1—H1A
C1—C2
C2—H2
C2—C3
C3—H3
C4—C3
C4—H4
C5—O1
C5—C4
C6—C1
C6—C5
C7—N1
C7—C6
C7—H7
C8—H8
C8—C9
C9—H9
C9—C10
C10—H10
C11—C10
1.384 (3)
1.401 (3)
0.9300
C13—C12
C14—H14
C14—C15
C15—H15
C16—C15
C16—H16
C16—C17
C17—H17
C18—C17
C18—H18
C19—C14
C19—C18
C20—H20
C20—C21
C21—H21
C22—C21
C22—H22
C23—C22
C23—H23
C24—C23
C24—H24
C25—C20
C25—C24
0.8600
1.387 (3)
0.9300
1.390 (3)
0.9300
1.387 (3)
0.9300
1.356 (4)
0.9300
1.366 (4)
0.9300
1.357 (4)
0.9300
1.368 (3)
0.9300
1.390 (3)
0.9300
1.352 (2)
1.385 (3)
1.380 (3)
1.391 (3)
1.454 (2)
1.521 (3)
0.9800
1.382 (3)
1.377 (3)
0.9300
1.391 (3)
0.9300
1.363 (4)
0.9300
0.9300
1.355 (4)
0.9300
1.387 (3)
0.9300
1.381 (3)
0.9300
1.374 (4)
0.9300
1.374 (3)
1.376 (3)
1.368 (4)
O2—P1—C7
O2—P1—C19
O2—P1—C25
C19—P1—C7
C25—P1—C7
C25—P1—C19
C5—O1—H1B
C7—N1—H1
C13—N1—H1
C13—N1—C7
C2—C1—H1A
C6—C1—H1A
C6—C1—C2
C1—C2—H2
C3—C2—C1
C3—C2—H2
C2—C3—H3
C2—C3—C4
C4—C3—H3
C3—C4—H4
110.33 (9)
110.55 (9)
114.61 (9)
108.59 (9)
105.28 (9)
107.19 (9)
109.5
C10—C11—C12
C12—C11—H11
C11—C12—H12
C11—C12—C13
C13—C12—H12
N1—C13—C12
C8—C13—N1
120.9 (2)
119.6
119.9
120.3 (2)
119.9
119.1 (2)
122.41 (17)
118.4 (2)
119.9
119.6
C8—C13—C12
C15—C14—H14
C19—C14—H14
C19—C14—C15
C14—C15—H15
C16—C15—C14
C16—C15—H15
C15—C16—H16
C15—C16—C17
C17—C16—H16
C16—C17—H17
C16—C17—C18
C18—C17—H17
119.6
120.81 (16)
119.6
119.9
120.2 (3)
120.0
119.6
120.7 (2)
120.3
120.0 (3)
120.0
119.5 (2)
120.3
119.7
120.6 (3)
119.7
119.4
121.1 (2)
119.4
119.8
120.3 (3)
119.8
120.2
Acta Cryst. (2013). C69, 1070-1072
sup-4

supplementary materials
C3—C4—C5
C5—C4—H4
O1—C5—C4
O1—C5—C6
C4—C5—C6
C1—C6—C5
C1—C6—C7
C5—C6—C7
P1—C7—H7
N1—C7—P1
N1—C7—C6
N1—C7—H7
C6—C7—P1
C6—C7—H7
C9—C8—H8
C13—C8—H8
C13—C8—C9
C8—C9—H9
C10—C9—C8
C10—C9—H9
C9—C10—H10
C11—C10—C9
C11—C10—H10
C10—C11—H11
119.6 (2)
120.2
C17—C18—H18
C19—C18—C17
C19—C18—H18
C14—C19—P1
C18—C19—P1
C18—C19—C14
C21—C20—H20
C25—C20—H20
C25—C20—C21
C20—C21—H21
C22—C21—C20
C22—C21—H21
C21—C22—H22
C23—C22—C21
C23—C22—H22
C22—C23—H23
C22—C23—C24
C24—C23—H23
C23—C24—H24
C25—C24—C23
C25—C24—H24
C20—C25—P1
C20—C25—C24
C24—C25—P1
120.1
119.9 (3)
120.1
123.9 (2)
115.74 (18)
120.4 (2)
118.79 (19)
122.05 (18)
119.09 (18)
107.8
124.35 (17)
116.58 (17)
119.1 (2)
119.9
119.9
120.1 (3)
119.9
108.69 (13)
116.05 (16)
107.8
120.2 (3)
119.9
108.47 (13)
107.8
119.9
120.2 (2)
119.9
119.9
119.9
120.0
120.2 (2)
119.6
120.0 (3)
120.0
120.8 (3)
119.6
119.6
120.8 (2)
119.6
120.3
119.4 (2)
120.3
119.59 (17)
118.65 (19)
121.71 (16)
119.6
Hydrogen-bond geometry (Å, º)
D—H···A
D—H
H···A
D···A
D—H···A
O1—H1B···O2i
0.82
1.79
2.5677 (19)
159
Symmetry code: (i) x−1/2, y, −z+3/2.
Acta Cryst. (2013). C69, 1070-1072
sup-5