organic papers
o162
Mahimaidoss Baby Mariyatraet al. C26H22OP+C4H3O4ÿ DOI: 10.1107/S1600536803029404 Acta Cryst.(2004). E60, o162±o164Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
Benzoylmethyltriphenylphosphonium
hydrogen maleate: supramolecular layer
formation due to CÐH
O interactions
Mahimaidoss Baby Mariyatra,a
Elinor C. Spencer,b
Krishanaswamy
Panchanatheswarana* and
Judith A. K. Howardb
aDepartment of Chemistry, Bharathidasan
University, Tiruchirappalli 620 024, Tamil Nadu, India, andbDepartment of Chemistry,
Durham University, Durham DH1 3LE, England Correspondence e-mail:
panch_45@yahoo.co.in
Key indicators
Single-crystal X-ray study
T= 120 K
Mean(C±C) = 0.003 AÊ
Rfactor = 0.041
wRfactor = 0.106
Data-to-parameter ratio = 13.4
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved
The molecule of the title salt, C26H22OP+.C4H3O4ÿ, consists of
a benzoylmethyltriphenylphosphonium cation (HBPPY) and
a hydrogen maleate anion. Owing to a strong OÐH O
intraionic hydrogen bond, each hydrogen maleate ion forms a ring, described by the graph-set notation S11(7). Several CÐ
H O interactions are present between the cations and
anions and contribute to the stabilization of the crystal structure.
Comment
Resonance-stabilized ketophosphorus ylides containing basic carbon and oxygen sites undergo C-protonation readily with mineral acids (Antipin & Struchkov, 1984; Baby Mariyatraet
al., 2002a). The proton af®nity values of
benzoylmethyl-enetriphenylphosphorane (BPPY) have been determined using PM3 calculations and reveal that C-protonation is energetically more favourable than O-protonation by only
13 kJ molÿ1 (Laavanya, 2002). By varying the anionic
component of this salt we have attempted to obtain the O-protonated form of the benzoylmethyltriphenylphospho-nium cation. Mineral acids and some hydrated metal salts are known to C-protonate the ylide, BPPY, forming the corres-ponding phosphonium salts and the phosphonium metalates respectively (Baby Mariyatraet al., 2002a,b, 2003; Albaneseet
al., 1989). To investigate the in¯uence of some dicarboxylic
acids on the mode of protonation, the reaction of maleic acid with BPPY has been performed. The formation of benzoyl-methyltriphenylphosphonium hydrogen maleate, (I), was con®rmed by single-crystal X-ray diffraction.
The solid-state structure of the title salt, (I) (Fig. 1), comprises of benzoylmethyltriphenylphosphonium cations and hydrogen maleate anions. The presence of COOH and
COOÿgroups in the hydrogen maleate ion is indicated by a
pair of CÐO bond lengths (C27ÐO2 and C27ÐO3) which differ by 0.078 (2) AÊ and by the corresponding bond lengths at C30 with a difference of 0.055 (2) AÊ (Table 1). The stability of the hydrogen maleate ion is ascribed to the presence of a
strong O2ÐH1 O5 hydrogen bond (Table 2). The location
of two H atoms, H8A and H8B, and the angle H8AÐC8Ð
H8Bof 106.4 (16)con®rms C8 as the site of protonation. The
P1ÐC8, C7ÐO1 and C8ÐC7 distances of 1.8020 (16),
1.2198 (19) and 1.516 (2) AÊ, respectively, are comparable with those of the previously reported phosphonium salts (Baby
Mariyatraet al., 2002a,b, 2003). The O1ÐC7ÐC8ÐP1 torsion
angle ofÿ11.78 (19)shows the near-coplanarity of the P and
O centres.
In the crystal structure, the phosphonium cations are
interlinked through CÐH O interactions between one of
the methylene H atoms and the benzoyl O atom of the
neighbouring phosphonium cation at (xÿ1
2, y, 12ÿz). The
HBPPY cations and the hydrogen maleate anions are
connected through CÐH O interactions, forming
close-packed zigzag layers in thebcplane (Table 2 and Fig. 2). Both
the methylene H8A and H8B atoms are involved in the
interionic CÐH O interactions (Fig. 3). Atom H8Bforms a
bifurcated hydrogen bond with O4 and O5 of the hydro-genmaleate ion at (1ÿx,ÿy, 1ÿz). A CÐH interaction
of 2.79 (2) AÊ between H25 and Cg1(ÿx, 1ÿy, ÿz) also
contributes to the intermolecular interactions,Cg1 being the
centroid of the aromatic ring of the benzoyl group (C1±C6).
Experimental
The title compound, (I), was prepared by warming BPPY (0.40 g, 1.05 mmol) and maleic acid (0.12 g, 1.03 mmol) in methanol. Diffraction-quality crystals were obtained by slow evaporation of the solvent.
Crystal data
C26H22OP+C4H3O4ÿ
Mr= 496.47
Orthorhombic,Pbca a= 10.5582 (5) AÊ b= 19.5961 (8) AÊ c= 24.0030 (11) AÊ V= 4966.2 (4) AÊ3
Z= 8
Dx= 1.328 Mg mÿ3
MoKradiation Cell parameters from 973
re¯ections = 2.2±27.0 = 0.15 mmÿ1
T= 120 (2) K Block, colourless 0.340.290.17 mm
Data collection
Bruker SMART 6K CCD area-detector diffractometer !scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1998a) Tmin= 0.820,Tmax= 0.975
36772 measured re¯ections
5704 independent re¯ections 4255 re¯ections withI> 2(I) Rint= 0.051
max= 27.5
h=ÿ13!11 k=ÿ25!23 l=ÿ31!30
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.041
wR(F2) = 0.106
S= 1.01 5704 re¯ections 425 parameters
All H-atom parameters re®ned
w= 1/[2(F
o2) + (0.0326P)2
+ 2.7423P]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001
max= 0.34 e AÊÿ3
min=ÿ0.26 e AÊÿ3
Acta Cryst.(2004). E60, o162±o164 Mahimaidoss Baby Mariyatraet al. C26H22OP+C4H3O4ÿ
o163
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Figure 2
The crystal structure of (I), projected along theaaxis.
Figure 3
Diagram showing the intermolecular interactions in the structure of (I). [Symmetry codes: (i)3
2ÿx,ÿy,12+z; (ii) 1ÿx, yÿ12,32ÿz; (iii)xÿ12,y, 3
2ÿz; (iv) 1ÿx,ÿy, 1ÿz; (v)xÿ12,12ÿy, 1ÿz.] Figure 1
organic papers
o164
Mahimaidoss Baby Mariyatraet al. C26H22OP+C4H3O4ÿ Acta Cryst.(2004). E60, o162±o164Table 1
Selected geometric parameters (AÊ,).
P1ÐC8 1.8020 (16) C7ÐO1 1.2198 (19) C7ÐC8 1.516 (2) C27ÐO3 1.221 (2)
C27ÐO2 1.299 (2) C30ÐO4 1.233 (2) C30ÐO5 1.288 (2)
C7ÐC8ÐP1 112.26 (11) O3ÐC27ÐO2 121.51 (19) O3ÐC27ÐC28 119.36 (17) O2ÐC27ÐC28 119.13 (17)
O4ÐC30ÐO5 122.85 (17) O4ÐC30ÐC29 118.13 (17) O5ÐC30ÐC29 119.02 (16)
O1ÐC7ÐC8ÐP1 ÿ11.78 (19) C27ÐC28ÐC29ÐC30 2.7 (3)
Table 2
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
C3ÐH3 O2i 0.94 (2) 2.44 (2) 3.243 (2) 143.0 (16)
C4ÐH4 O3ii 0.98 (2) 2.36 (2) 3.277 (2) 156.8 (16)
C8ÐH8A O1iii 0.984 (19) 2.397 (19) 3.371 (2) 170.3 (15)
C8ÐH8B O4iv 1.00 (2) 2.42 (2) 3.184 (2) 132.9 (16)
C8ÐH8B O5iv 1.00 (2) 2.28 (2) 3.270 (2) 171.0 (17)
C26ÐH26 O4iv 0.98 (2) 2.494 (19) 3.267 (2) 135.4 (15)
C19ÐH19 O4v 0.93 (2) 2.49 (2) 3.210 (2) 134.8 (19)
C26ÐH26 O1 0.98 (2) 2.47 (2) 3.042 (2) 117.1 (14) O2ÐH1 O5 1.07 (3) 1.35 (3) 2.4197 (19) 176 (3) Symmetry codes: (i) 3
2ÿx;ÿy;21z; (ii) 1ÿx;yÿ21;32ÿz; (iii) xÿ12;y;32ÿz; (iv)
1ÿx;ÿy;1ÿz; (v)xÿ1
2;12ÿy;1ÿz.
All H atoms were located in difference Fourier maps, and their positional andUisoparameters were re®ned. The CÐH bond lengths
are in the range 0.92 (2)±1.00 (2) AÊ.
Data collection:SMART(Bruker, 1998); cell re®nement:SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure:SHELXTL(Sheldrick, 1998b); program(s) used to re®ne structure:SHELXTL; molecular graphics:SHELXTL; software used to prepare material for publication:SHELXTL.
ECS thanks the EPSRC for support.
References
Albanese, J. A., Staley, D. L., Rheingold, A. L. & Burmeister, J. L. (1989).Acta Cryst.C45, 1128±1131.
Antipin, M. Yu. & Struchkov, Yu. T. (1984).Zh. Strukt. Khim.25, 122±131. Baby Mariyatra, M., Panchanatheswaran, K. & Goeta, A. E. (2002a).Acta
Cryst.E58, o807±o809.
Baby Mariyatra, M., Panchanatheswaran, K. & Goeta, A. E. (2002b).Acta Cryst.E58, m694±m696.
Baby Mariyatra, M., Panchanatheswaran, K. & Goeta, A. E. (2003).Acta Cryst.E59, o255±o257.
Bruker (1998).SMART-NTandSAINT-NT. Versions 5.0. Bruker AXS Inc., Madison, Wisconsin, USA.
Laavanya, P. (2002). PhD Thesis, Bharathidasan University, India. Sheldrick, G. M. (1998a).SADABS. University of GoÈttingen, Germany. Sheldrick, G. M. (1998b).SHELXTL.Bruker AXS Inc., Madison, Wisconsin,
supporting information
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Acta Cryst. (2004). E60, o162–o164
supporting information
Acta Cryst. (2004). E60, o162–o164 [https://doi.org/10.1107/S1600536803029404]
Benzoylmethyltriphenylphosphonium hydrogen maleate: supramolecular layer
formation due to C
—
H
···
O interactions
Mahimaidoss Baby Mariyatra, Elinor C. Spencer, Krishanaswamy Panchanatheswaran and Judith
A. K. Howard
Benzoylmethyltriphenylphosphonium hydrogenmaleate
Crystal data
C26H22OP+·C4H3O4− Mr = 496.47
Orthorhombic, Pbca Hall symbol: -P 2ac 2ab a = 10.5582 (5) Å b = 19.5961 (8) Å c = 24.0030 (11) Å V = 4966.2 (4) Å3 Z = 8
F(000) = 2080
Dx = 1.328 Mg m−3 Melting point: 413 K
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 973 reflections θ = 2.3–27.0°
µ = 0.15 mm−1 T = 120 K Block, colourless 0.34 × 0.29 × 0.17 mm
Data collection
Bruker SMART CCD 6K area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
Detector resolution: 8 pixels mm-1 ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) Tmin = 0.820, Tmax = 0.975
36772 measured reflections 5704 independent reflections 4255 reflections with I > 2σ(I) Rint = 0.051
θmax = 27.5°, θmin = 1.7° h = −13→11
k = −25→23 l = −31→30
Refinement
Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.041 wR(F2) = 0.106 S = 1.01 5704 reflections 425 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: difference Fourier map All H-atom parameters refined
w = 1/[σ2(F
o2) + (0.0326P)2 + 2.7423P] where P = (Fo2 + 2Fc2)/3
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Acta Cryst. (2004). E60, o162–o164 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.
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 0.07926 (4) 0.08182 (2) 0.668013 (17) 0.02209 (11)
C1 0.12537 (15) −0.05703 (8) 0.79639 (7) 0.0244 (3)
C2 0.20776 (17) −0.05985 (10) 0.84150 (8) 0.0346 (4)
H2 0.277 (2) −0.0297 (11) 0.8435 (9) 0.051 (6)*
C3 0.18939 (18) −0.10682 (11) 0.88364 (8) 0.0387 (4)
H3 0.246 (2) −0.1095 (10) 0.9141 (9) 0.041 (6)*
C4 0.08858 (19) −0.15212 (9) 0.88077 (8) 0.0367 (4)
H4 0.0750 (18) −0.1864 (9) 0.9096 (8) 0.034 (5)*
C5 0.0062 (2) −0.14953 (10) 0.83594 (8) 0.0382 (4)
H5 −0.067 (2) −0.1793 (11) 0.8332 (10) 0.052 (6)*
C6 0.02354 (17) −0.10196 (9) 0.79383 (8) 0.0316 (4)
H6 −0.0353 (18) −0.1012 (9) 0.7623 (8) 0.032 (5)*
C7 0.14983 (14) −0.00508 (8) 0.75298 (7) 0.0233 (3)
C8 0.05025 (15) 0.00587 (8) 0.70838 (7) 0.0225 (3)
H8A −0.0353 (18) 0.0105 (9) 0.7243 (8) 0.030 (5)*
H8B 0.047 (2) −0.0345 (11) 0.6831 (9) 0.046 (6)*
C9 −0.05591 (15) 0.09462 (8) 0.62374 (7) 0.0272 (4)
C10 −0.0781 (2) 0.04718 (10) 0.58145 (8) 0.0390 (4)
H10 −0.023 (2) 0.0102 (11) 0.5773 (9) 0.043 (6)*
C11 −0.1790 (2) 0.05661 (12) 0.54539 (10) 0.0482 (5)
H11 −0.192 (2) 0.0248 (12) 0.5178 (10) 0.053 (7)*
C12 −0.25651 (19) 0.11300 (12) 0.55126 (9) 0.0484 (6)
H12 −0.325 (2) 0.1194 (11) 0.5241 (10) 0.050 (6)*
C13 −0.2350 (2) 0.15959 (13) 0.59294 (10) 0.0508 (6)
H13 −0.290 (2) 0.1981 (12) 0.5972 (11) 0.065 (7)*
C14 −0.13463 (18) 0.15106 (11) 0.62964 (8) 0.0386 (4)
H14 −0.119 (2) 0.1856 (12) 0.6584 (10) 0.055 (7)*
C15 0.09654 (15) 0.15199 (8) 0.71576 (7) 0.0259 (3)
C16 0.01554 (18) 0.15627 (10) 0.76133 (9) 0.0378 (4)
H16 −0.051 (2) 0.1243 (10) 0.7644 (9) 0.044 (6)*
C17 0.03165 (19) 0.20852 (11) 0.79980 (10) 0.0444 (5)
H17 −0.023 (2) 0.2102 (12) 0.8326 (11) 0.061 (7)*
C18 0.12595 (19) 0.25625 (10) 0.79270 (9) 0.0388 (4)
H18 0.1354 (19) 0.2917 (10) 0.8194 (9) 0.041 (6)*
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Acta Cryst. (2004). E60, o162–o164
H19 0.269 (2) 0.2850 (11) 0.7412 (10) 0.056 (7)*
C20 0.19149 (17) 0.20035 (9) 0.70861 (8) 0.0311 (4)
H20 0.249 (2) 0.1979 (10) 0.6772 (9) 0.036 (5)*
C21 0.21235 (14) 0.07272 (8) 0.62209 (7) 0.0249 (3)
C22 0.22264 (18) 0.11835 (9) 0.57764 (7) 0.0314 (4)
H22 0.1616 (19) 0.1536 (10) 0.5732 (8) 0.038 (5)*
C23 0.3218 (2) 0.11160 (9) 0.53999 (8) 0.0376 (4)
H23 0.326 (2) 0.1429 (11) 0.5081 (9) 0.048 (6)*
C24 0.40862 (18) 0.05970 (10) 0.54626 (8) 0.0379 (4)
H24 0.477 (2) 0.0556 (11) 0.5197 (10) 0.048 (6)*
C25 0.39807 (18) 0.01380 (11) 0.58970 (8) 0.0390 (4)
H25 0.458 (2) −0.0218 (11) 0.5930 (9) 0.046 (6)*
C26 0.29967 (16) 0.01984 (9) 0.62795 (8) 0.0328 (4)
H26 0.2923 (18) −0.0142 (10) 0.6578 (8) 0.034 (5)*
C27 1.00604 (18) 0.21784 (9) 0.48101 (8) 0.0376 (4)
C28 0.87176 (18) 0.21626 (9) 0.46199 (8) 0.0326 (4)
H28 0.8221 (18) 0.2422 (10) 0.4850 (9) 0.038 (5)*
C29 0.81817 (18) 0.18673 (9) 0.41798 (8) 0.0325 (4)
H29 0.729 (2) 0.1930 (10) 0.4135 (9) 0.042 (6)*
C30 0.87435 (17) 0.14243 (9) 0.37351 (8) 0.0314 (4)
O1 0.24667 (11) 0.02886 (6) 0.75232 (5) 0.0298 (3)
O2 1.08911 (13) 0.18012 (8) 0.45561 (7) 0.0507 (4)
H1 1.043 (3) 0.1521 (16) 0.4232 (14) 0.097 (10)*
O3 1.03557 (14) 0.25455 (8) 0.51998 (7) 0.0559 (4)
O4 0.80859 (13) 0.12865 (7) 0.33260 (6) 0.0406 (3)
O5 0.98781 (12) 0.11955 (7) 0.37990 (6) 0.0417 (3)
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
P1 0.01906 (19) 0.0239 (2) 0.0233 (2) 0.00029 (15) −0.00039 (15) 0.00196 (16)
C1 0.0225 (8) 0.0283 (8) 0.0222 (8) 0.0032 (6) 0.0021 (6) 0.0011 (6)
C2 0.0220 (8) 0.0507 (11) 0.0312 (10) −0.0017 (8) −0.0007 (7) 0.0101 (8)
C3 0.0275 (9) 0.0593 (12) 0.0293 (10) 0.0064 (8) −0.0013 (8) 0.0140 (9)
C4 0.0443 (11) 0.0348 (9) 0.0308 (10) 0.0081 (8) 0.0082 (8) 0.0100 (8)
C5 0.0470 (11) 0.0340 (9) 0.0336 (10) −0.0104 (8) 0.0032 (9) 0.0030 (8)
C6 0.0349 (10) 0.0330 (9) 0.0268 (9) −0.0054 (7) −0.0026 (7) 0.0011 (7)
C7 0.0210 (8) 0.0266 (8) 0.0225 (8) 0.0026 (6) 0.0010 (6) −0.0001 (6)
C8 0.0214 (8) 0.0247 (8) 0.0215 (8) −0.0005 (6) −0.0003 (6) 0.0026 (6)
C9 0.0217 (8) 0.0327 (8) 0.0271 (9) −0.0035 (6) −0.0025 (6) 0.0081 (7)
C10 0.0409 (11) 0.0348 (10) 0.0413 (11) −0.0043 (8) −0.0135 (9) 0.0052 (8)
C11 0.0517 (13) 0.0474 (12) 0.0453 (13) −0.0188 (10) −0.0207 (10) 0.0093 (10)
C12 0.0281 (10) 0.0718 (15) 0.0453 (13) −0.0107 (10) −0.0102 (9) 0.0245 (11)
C13 0.0311 (11) 0.0746 (15) 0.0465 (13) 0.0174 (11) −0.0031 (9) 0.0132 (11)
C14 0.0308 (10) 0.0502 (11) 0.0347 (10) 0.0111 (8) −0.0017 (8) 0.0032 (9)
C15 0.0234 (8) 0.0247 (8) 0.0298 (9) 0.0038 (6) −0.0023 (6) −0.0001 (6)
C16 0.0277 (9) 0.0428 (10) 0.0430 (11) −0.0047 (8) 0.0067 (8) −0.0121 (9)
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Acta Cryst. (2004). E60, o162–o164
C18 0.0402 (11) 0.0329 (9) 0.0432 (11) 0.0053 (8) −0.0106 (9) −0.0099 (9)
C19 0.0431 (11) 0.0286 (9) 0.0411 (11) −0.0060 (8) −0.0111 (9) 0.0033 (8)
C20 0.0304 (9) 0.0316 (9) 0.0313 (10) −0.0016 (7) −0.0034 (7) 0.0043 (7)
C21 0.0228 (8) 0.0290 (8) 0.0229 (8) −0.0032 (6) 0.0015 (6) −0.0007 (6)
C22 0.0396 (10) 0.0276 (8) 0.0270 (9) −0.0007 (7) 0.0025 (7) 0.0010 (7)
C23 0.0525 (12) 0.0304 (9) 0.0298 (10) −0.0083 (8) 0.0121 (8) −0.0004 (8)
C24 0.0358 (10) 0.0434 (10) 0.0344 (10) −0.0098 (8) 0.0135 (8) −0.0096 (8)
C25 0.0288 (10) 0.0477 (11) 0.0405 (11) 0.0071 (8) 0.0049 (8) −0.0027 (9)
C26 0.0275 (9) 0.0381 (10) 0.0328 (10) 0.0054 (7) 0.0034 (7) 0.0046 (8)
C27 0.0376 (10) 0.0373 (10) 0.0378 (10) 0.0019 (8) 0.0044 (8) −0.0075 (8)
C28 0.0341 (9) 0.0279 (9) 0.0358 (10) 0.0047 (7) 0.0089 (8) −0.0015 (7)
C29 0.0293 (9) 0.0313 (9) 0.0369 (10) 0.0054 (7) 0.0071 (7) 0.0024 (7)
C30 0.0352 (9) 0.0275 (8) 0.0316 (10) 0.0017 (7) 0.0051 (8) 0.0033 (7)
O1 0.0219 (6) 0.0354 (6) 0.0320 (6) −0.0043 (5) −0.0018 (5) 0.0051 (5)
O2 0.0348 (8) 0.0650 (10) 0.0525 (9) 0.0128 (7) −0.0034 (6) −0.0270 (8)
O3 0.0452 (9) 0.0655 (10) 0.0571 (10) 0.0014 (7) 0.0001 (7) −0.0298 (8)
O4 0.0445 (8) 0.0421 (7) 0.0353 (8) 0.0059 (6) −0.0030 (6) −0.0025 (6)
O5 0.0350 (7) 0.0455 (8) 0.0446 (8) 0.0121 (6) −0.0007 (6) −0.0152 (6)
Geometric parameters (Å, º)
P1—C21 1.7949 (16) C15—C16 1.391 (3)
P1—C9 1.7970 (16) C16—C17 1.389 (3)
P1—C15 1.7993 (17) C16—H16 0.95 (2)
P1—C8 1.8020 (16) C17—C18 1.377 (3)
C1—C2 1.390 (2) C17—H17 0.98 (3)
C1—C6 1.391 (2) C18—C19 1.375 (3)
C1—C7 1.480 (2) C18—H18 0.95 (2)
C2—C3 1.381 (3) C19—C20 1.394 (3)
C2—H2 0.94 (2) C19—H19 0.93 (2)
C3—C4 1.388 (3) C20—H20 0.97 (2)
C3—H3 0.94 (2) C21—C26 1.394 (2)
C4—C5 1.385 (3) C21—C22 1.396 (2)
C4—H4 0.98 (2) C22—C23 1.389 (3)
C5—C6 1.387 (3) C22—H22 0.95 (2)
C5—H5 0.97 (2) C23—C24 1.378 (3)
C6—H6 0.98 (2) C23—H23 0.98 (2)
C7—O1 1.2198 (19) C24—C25 1.382 (3)
C7—C8 1.516 (2) C24—H24 0.96 (2)
C8—H8A 0.984 (19) C25—C26 1.391 (3)
C8—H8B 1.00 (2) C25—H25 0.95 (2)
C9—C14 1.391 (3) C26—H26 0.98 (2)
C9—C10 1.396 (3) C27—O3 1.221 (2)
C10—C11 1.385 (3) C27—O2 1.299 (2)
C10—H10 0.93 (2) C27—C28 1.490 (3)
C11—C12 1.382 (3) C28—C29 1.331 (3)
C11—H11 0.92 (2) C28—H28 0.92 (2)
supporting information
sup-5
Acta Cryst. (2004). E60, o162–o164
C12—H12 0.98 (2) C29—H29 0.96 (2)
C13—C14 1.388 (3) C30—O4 1.233 (2)
C13—H13 0.96 (2) C30—O5 1.288 (2)
C14—H14 0.98 (2) O2—H1 1.07 (3)
C15—C20 1.390 (2)
C21—P1—C9 105.81 (8) C9—C14—H14 121.4 (14)
C21—P1—C15 112.81 (8) C20—C15—C16 119.96 (16)
C9—P1—C15 110.52 (8) C20—C15—P1 121.03 (13)
C21—P1—C8 112.41 (8) C16—C15—P1 118.98 (13)
C9—P1—C8 107.36 (7) C17—C16—C15 119.46 (18)
C15—P1—C8 107.81 (8) C17—C16—H16 121.8 (13)
C2—C1—C6 119.54 (16) C15—C16—H16 118.7 (13)
C2—C1—C7 117.82 (15) C18—C17—C16 120.46 (19)
C6—C1—C7 122.64 (15) C18—C17—H17 120.3 (14)
C3—C2—C1 120.60 (18) C16—C17—H17 119.2 (14)
C3—C2—H2 119.4 (14) C19—C18—C17 120.33 (18)
C1—C2—H2 120.0 (14) C19—C18—H18 120.4 (13)
C2—C3—C4 119.84 (18) C17—C18—H18 119.3 (13)
C2—C3—H3 121.1 (13) C18—C19—C20 120.07 (18)
C4—C3—H3 119.1 (13) C18—C19—H19 122.0 (14)
C5—C4—C3 119.81 (17) C20—C19—H19 117.9 (15)
C5—C4—H4 119.0 (12) C15—C20—C19 119.71 (18)
C3—C4—H4 121.2 (12) C15—C20—H20 120.8 (12)
C4—C5—C6 120.52 (18) C19—C20—H20 119.5 (12)
C4—C5—H5 122.0 (14) C26—C21—C22 120.11 (16)
C6—C5—H5 117.4 (14) C26—C21—P1 121.98 (13)
C5—C6—C1 119.69 (17) C22—C21—P1 117.81 (13)
C5—C6—H6 119.3 (11) C23—C22—C21 119.65 (17)
C1—C6—H6 121.0 (11) C23—C22—H22 120.4 (12)
O1—C7—C1 122.05 (14) C21—C22—H22 119.9 (12)
O1—C7—C8 119.67 (14) C24—C23—C22 120.05 (18)
C1—C7—C8 118.28 (13) C24—C23—H23 121.0 (13)
C7—C8—P1 112.26 (11) C22—C23—H23 118.9 (13)
C7—C8—H8A 112.1 (11) C23—C24—C25 120.63 (17)
P1—C8—H8A 106.7 (10) C23—C24—H24 119.1 (13)
C7—C8—H8B 109.8 (12) C25—C24—H24 120.3 (13)
P1—C8—H8B 109.4 (12) C24—C25—C26 120.18 (18)
H8A—C8—H8B 106.4 (16) C24—C25—H25 119.3 (13)
C14—C9—C10 120.22 (17) C26—C25—H25 120.5 (13)
C14—C9—P1 121.70 (14) C25—C26—C21 119.37 (17)
C10—C9—P1 118.05 (13) C25—C26—H26 118.9 (11)
C11—C10—C9 119.6 (2) C21—C26—H26 121.7 (11)
C11—C10—H10 120.9 (13) O3—C27—O2 121.51 (19)
C9—C10—H10 119.5 (13) O3—C27—C28 119.36 (17)
C12—C11—C10 119.9 (2) O2—C27—C28 119.13 (17)
C12—C11—H11 122.0 (14) C29—C28—C27 131.07 (17)
supporting information
sup-6
Acta Cryst. (2004). E60, o162–o164
C13—C12—C11 120.54 (19) C27—C28—H28 110.4 (12)
C13—C12—H12 121.4 (13) C28—C29—C30 130.47 (18)
C11—C12—H12 118.0 (13) C28—C29—H29 116.8 (12)
C12—C13—C14 120.5 (2) C30—C29—H29 112.7 (12)
C12—C13—H13 120.1 (15) O4—C30—O5 122.85 (17)
C14—C13—H13 119.3 (16) O4—C30—C29 118.13 (17)
C13—C14—C9 119.2 (2) O5—C30—C29 119.02 (16)
C13—C14—H14 119.4 (14) C27—O2—H1 109.1 (17)
C6—C1—C2—C3 0.1 (3) C9—P1—C15—C20 −106.19 (14)
C7—C1—C2—C3 179.44 (17) C8—P1—C15—C20 136.75 (14)
C1—C2—C3—C4 0.6 (3) C21—P1—C15—C16 −166.01 (14)
C2—C3—C4—C5 −0.6 (3) C9—P1—C15—C16 75.76 (16)
C3—C4—C5—C6 0.0 (3) C8—P1—C15—C16 −41.29 (16)
C4—C5—C6—C1 0.7 (3) C20—C15—C16—C17 −0.9 (3)
C2—C1—C6—C5 −0.7 (3) P1—C15—C16—C17 177.15 (16)
C7—C1—C6—C5 179.92 (16) C15—C16—C17—C18 0.8 (3)
C2—C1—C7—O1 9.0 (2) C16—C17—C18—C19 −0.4 (3)
C6—C1—C7—O1 −171.66 (16) C17—C18—C19—C20 0.2 (3)
C2—C1—C7—C8 −170.76 (15) C16—C15—C20—C19 0.7 (3)
C6—C1—C7—C8 8.6 (2) P1—C15—C20—C19 −177.30 (14)
O1—C7—C8—P1 −11.78 (19) C18—C19—C20—C15 −0.4 (3)
C1—C7—C8—P1 167.98 (11) C9—P1—C21—C26 −131.84 (15)
C21—P1—C8—C7 71.77 (13) C15—P1—C21—C26 107.21 (15)
C9—P1—C8—C7 −172.28 (11) C8—P1—C21—C26 −14.96 (17)
C15—P1—C8—C7 −53.19 (13) C9—P1—C21—C22 44.54 (15)
C21—P1—C9—C14 −124.73 (15) C15—P1—C21—C22 −76.41 (15)
C15—P1—C9—C14 −2.30 (17) C8—P1—C21—C22 161.42 (13)
C8—P1—C9—C14 115.04 (15) C26—C21—C22—C23 −1.3 (3)
C21—P1—C9—C10 53.15 (16) P1—C21—C22—C23 −177.76 (14)
C15—P1—C9—C10 175.57 (14) C21—C22—C23—C24 0.6 (3)
C8—P1—C9—C10 −67.09 (16) C22—C23—C24—C25 0.2 (3)
C14—C9—C10—C11 0.0 (3) C23—C24—C25—C26 −0.4 (3)
P1—C9—C10—C11 −177.92 (16) C24—C25—C26—C21 −0.2 (3)
C9—C10—C11—C12 0.4 (3) C22—C21—C26—C25 1.1 (3)
C10—C11—C12—C13 −0.6 (3) P1—C21—C26—C25 177.40 (14)
C11—C12—C13—C14 0.4 (3) O3—C27—C28—C29 172.3 (2)
C12—C13—C14—C9 −0.1 (3) O2—C27—C28—C29 −7.6 (3)
C10—C9—C14—C13 −0.1 (3) C27—C28—C29—C30 2.7 (3)
P1—C9—C14—C13 177.68 (16) C28—C29—C30—O4 −170.25 (19)
C21—P1—C15—C20 12.04 (16) C28—C29—C30—O5 10.8 (3)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
C3—H3···O2i 0.94 (2) 2.44 (2) 3.243 (2) 143.0 (16)
C4—H4···O3ii 0.98 (2) 2.36 (2) 3.277 (2) 156.8 (16)
supporting information
sup-7
Acta Cryst. (2004). E60, o162–o164
C8—H8B···O4iv 1.00 (2) 2.42 (2) 3.184 (2) 132.9 (16)
C8—H8B···O5iv 1.00 (2) 2.28 (2) 3.270 (2) 171.0 (17)
C26—H26···O4iv 0.98 (2) 2.494 (19) 3.267 (2) 135.4 (15)
C19—H19···O4v 0.93 (2) 2.49 (2) 3.210 (2) 134.8 (19)
C26—H26···O1 0.98 (2) 2.47 (2) 3.042 (2) 117.1 (14)
O2—H1···O5 1.07 (3) 1.35 (3) 2.4197 (19) 176 (3)