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Hydrogen bonding and crystal packing play major roles in determining the conformations of ethyl methyl 2-(triphenyl­phospho­ranyl­idene)malonate, Ph3P=C(CO2CH3)CO2CH2CH3 or C24H23O4P, (I), and dimethyl 2-(triphenyl­phosphor­anyl­idene)malonate, Ph3P=C(CO2CH3)2 or C23H21O4P, (II). In (I), the acyl O atom of the ethyl ester group is anti to the P atom, while the O atom of the methyl ester group is syn. In (II), the dimethyl diester is a 1:1 mixture of anti-anti and syn-anti conformers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107010542/sq3064sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107010542/sq3064Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107010542/sq3064IIsup3.hkl
Contains datablock II

CCDC references: 645589; 645590

Computing details top

For both compounds, data collection: SMART-NT (Bruker, 2001); cell refinement: SAINT-NT (Bruker, 2001 ); data reduction: SAINT-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Bruker, 2001); software used to prepare material for publication: SHELXTL-NT and PLATON (Spek, 2003).

(I) methyl ethyl 2-(triphenylphosphoranylidene)malonate top
Crystal data top
C24H23O4PF(000) = 856
Mr = 406.39Dx = 1.285 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5668 reflections
a = 14.3378 (17) Åθ = 2.6–27.0°
b = 9.1666 (11) ŵ = 0.16 mm1
c = 16.2696 (19) ÅT = 295 K
β = 100.711 (2)°Block, colourless
V = 2101.0 (4) Å30.20 × 0.18 × 0.14 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2769 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.061
Graphite monochromatorθmax = 28.0°, θmin = 1.7°
φ and ω scansh = 1817
17124 measured reflectionsk = 1111
4717 independent reflectionsl = 2021
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0625P)2]
where P = (Fo2 + 2Fc2)/3
4717 reflections(Δ/σ)max = 0.008
272 parametersΔρmax = 0.32 e Å3
34 restraintsΔρmin = 0.32 e Å3
Special details top

Experimental. 1H NMR (CDCl3, δ, p.p.m.): 0.75 (t, 3H, J = 7 Hz), 3.39 (s, 3H), 3.79 (q, 2H, J = 7 Hz), 7.5–8.0 (m, 15H). IR (KBr): 1666.1 and 1616.0 (CO) cm-1.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
P10.44976 (5)0.27189 (8)0.17940 (4)0.0426 (2)
O10.46992 (16)0.1093 (3)0.40156 (13)0.0762 (7)
O20.36472 (14)0.2502 (2)0.31977 (12)0.0567 (6)
O30.58270 (15)0.0162 (2)0.19209 (14)0.0730 (7)
O40.61944 (15)0.0130 (2)0.33139 (13)0.0707 (7)
C10.49027 (18)0.1568 (3)0.26359 (16)0.0429 (7)
C20.4371 (2)0.1776 (3)0.32872 (17)0.0476 (7)
C30.5696 (2)0.0586 (3)0.26900 (19)0.0492 (7)
C40.4129 (3)0.1323 (5)0.4673 (2)0.1041 (15)
H4A0.44080.07940.51670.156*
H4B0.34940.09800.44780.156*
H4C0.41150.23440.48010.156*
C5A0.6786 (2)0.0426 (5)0.1858 (3)0.0848 (17)0.804 (6)
H5A10.72570.00790.23240.102*0.804 (6)
H5A20.69660.00980.13430.102*0.804 (6)
C6A0.6738 (5)0.2069 (5)0.1872 (4)0.140 (3)0.804 (6)
H6A10.67030.23930.24270.209*0.804 (6)
H6A20.72960.24680.17090.209*0.804 (6)
H6A30.61850.23930.14890.209*0.804 (6)
C5B0.6459 (14)0.1154 (15)0.2005 (15)0.0848 (17)0.196 (6)
H5B10.61170.20250.17840.102*0.196 (6)
H5B20.67660.13210.25810.102*0.196 (6)
C6B0.7156 (18)0.066 (3)0.1471 (16)0.140 (3)0.196 (6)
H6B10.68990.08600.08930.209*0.196 (6)
H6B20.77430.11830.16330.209*0.196 (6)
H6B30.72690.03640.15460.209*0.196 (6)
C110.53019 (19)0.2768 (3)0.10623 (17)0.0456 (7)
C120.6149 (2)0.3521 (4)0.12467 (19)0.0637 (9)
H120.62830.40750.17330.076*
C130.6800 (2)0.3463 (4)0.0720 (2)0.0716 (10)
H130.73720.39620.08580.086*
C140.6606 (2)0.2678 (4)0.0001 (2)0.0680 (9)
H140.70480.26330.03510.082*
C150.5759 (2)0.1952 (4)0.0206 (2)0.0680 (9)
H150.56190.14330.07050.082*
C160.5114 (2)0.1992 (3)0.03270 (19)0.0587 (8)
H160.45440.14870.01860.070*
C210.33617 (19)0.2217 (3)0.11787 (16)0.0440 (7)
C220.2956 (2)0.3010 (3)0.04792 (18)0.0549 (8)
H220.32620.38370.03310.066*
C230.2100 (2)0.2587 (4)0.00013 (19)0.0653 (9)
H230.18240.31270.04670.078*
C240.1663 (2)0.1347 (4)0.0225 (2)0.0680 (10)
H240.10890.10500.00950.082*
C250.2059 (2)0.0551 (4)0.0907 (2)0.0640 (9)
H250.17550.02840.10480.077*
C260.2905 (2)0.0979 (3)0.13875 (18)0.0504 (7)
H260.31730.04340.18550.060*
C310.4442 (2)0.4553 (3)0.22059 (17)0.0463 (7)
C320.5195 (2)0.5011 (4)0.2813 (2)0.0678 (9)
H320.57010.43860.29990.081*
C330.5190 (3)0.6408 (4)0.3141 (2)0.0787 (11)
H330.57000.67240.35400.094*
C340.4442 (3)0.7321 (4)0.2883 (2)0.0744 (10)
H340.44440.82570.31030.089*
C350.3698 (3)0.6857 (4)0.2306 (2)0.0677 (9)
H350.31840.74750.21370.081*
C360.3691 (2)0.5473 (3)0.19629 (19)0.0569 (8)
H360.31740.51690.15660.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0431 (4)0.0373 (4)0.0454 (4)0.0001 (3)0.0032 (3)0.0028 (3)
O10.0772 (16)0.0970 (18)0.0577 (14)0.0394 (13)0.0210 (12)0.0301 (13)
O20.0536 (13)0.0574 (13)0.0585 (13)0.0184 (10)0.0084 (10)0.0076 (10)
O30.0826 (17)0.0738 (16)0.0631 (14)0.0381 (13)0.0149 (12)0.0020 (12)
O40.0623 (14)0.0813 (16)0.0606 (14)0.0291 (12)0.0088 (11)0.0014 (12)
C10.0387 (15)0.0426 (16)0.0451 (16)0.0064 (12)0.0018 (13)0.0012 (13)
C20.0497 (18)0.0436 (17)0.0459 (17)0.0038 (14)0.0004 (14)0.0049 (14)
C30.0469 (17)0.0463 (18)0.0533 (19)0.0048 (14)0.0062 (15)0.0016 (15)
C40.096 (3)0.149 (4)0.078 (2)0.062 (3)0.043 (2)0.056 (3)
C5A0.094 (4)0.077 (3)0.092 (3)0.036 (3)0.041 (3)0.013 (3)
C6A0.148 (5)0.135 (5)0.142 (5)0.034 (4)0.044 (4)0.013 (4)
C5B0.094 (4)0.077 (3)0.092 (3)0.036 (3)0.041 (3)0.013 (3)
C6B0.148 (5)0.135 (5)0.142 (5)0.034 (4)0.044 (4)0.013 (4)
C110.0455 (17)0.0414 (16)0.0470 (16)0.0050 (13)0.0014 (13)0.0036 (13)
C120.060 (2)0.076 (2)0.0546 (19)0.0194 (18)0.0096 (17)0.0096 (17)
C130.059 (2)0.086 (3)0.070 (2)0.0316 (19)0.0121 (18)0.000 (2)
C140.063 (2)0.082 (3)0.062 (2)0.0106 (19)0.0219 (18)0.0108 (19)
C150.065 (2)0.085 (3)0.055 (2)0.0178 (19)0.0152 (17)0.0101 (18)
C160.0492 (18)0.068 (2)0.0592 (19)0.0150 (16)0.0104 (15)0.0073 (16)
C210.0434 (16)0.0419 (16)0.0463 (16)0.0005 (13)0.0069 (13)0.0013 (13)
C220.0565 (19)0.0486 (19)0.0560 (18)0.0028 (15)0.0014 (15)0.0098 (15)
C230.066 (2)0.070 (2)0.0534 (19)0.0021 (18)0.0072 (16)0.0003 (17)
C240.0482 (19)0.085 (3)0.067 (2)0.0093 (19)0.0002 (17)0.018 (2)
C250.061 (2)0.063 (2)0.067 (2)0.0183 (17)0.0116 (18)0.0079 (18)
C260.0567 (19)0.0428 (17)0.0513 (17)0.0002 (14)0.0090 (15)0.0002 (14)
C310.0485 (17)0.0389 (16)0.0511 (17)0.0024 (14)0.0087 (14)0.0017 (13)
C320.061 (2)0.061 (2)0.079 (2)0.0010 (17)0.0063 (18)0.0193 (18)
C330.077 (3)0.067 (2)0.091 (3)0.016 (2)0.013 (2)0.026 (2)
C340.095 (3)0.0408 (19)0.096 (3)0.007 (2)0.038 (2)0.0099 (19)
C350.082 (3)0.047 (2)0.078 (2)0.0089 (18)0.024 (2)0.0100 (17)
C360.066 (2)0.0463 (18)0.0569 (19)0.0010 (16)0.0078 (16)0.0096 (15)
Geometric parameters (Å, º) top
P1—C11.741 (3)C13—C141.358 (4)
P1—C111.805 (3)C13—H130.9300
P1—C211.805 (3)C14—C151.371 (4)
P1—C311.817 (3)C14—H140.9300
O1—C21.345 (3)C15—C161.381 (4)
O1—C41.477 (4)C15—H150.9300
O2—C21.219 (3)C16—H160.9300
O3—C31.356 (3)C21—C261.384 (4)
O3—C5B1.4997 (11)C21—C221.384 (4)
O3—C5A1.4982 (10)C22—C231.382 (4)
O4—C31.203 (3)C22—H220.9300
C1—C21.428 (4)C23—C241.380 (4)
C1—C31.440 (4)C23—H230.9300
C4—H4A0.9600C24—C251.361 (4)
C4—H4B0.9600C24—H240.9300
C4—H4C0.9600C25—C261.373 (4)
C5A—C6A1.5084 (11)C25—H250.9300
C5A—H5A10.9700C26—H260.9300
C5A—H5A20.9700C31—C361.367 (4)
C6A—H6A10.9600C31—C321.386 (4)
C6A—H6A20.9600C32—C331.388 (4)
C6A—H6A30.9600C32—H320.9300
C5B—C6B1.5102 (11)C33—C341.363 (5)
C5B—H5B10.9700C33—H330.9300
C5B—H5B20.9700C34—C351.352 (5)
C6B—H6B10.96C34—H340.9300
C6B—H6B20.96C35—C361.385 (4)
C6B—H6B30.96C35—H350.9300
C11—C121.380 (4)C36—H360.9300
C11—C161.375 (4)P1—O22.789 (2)
C12—C131.381 (4)P1—O33.004 (2)
C12—H120.9300O1—O42.755 (3)
C1—P1—C11111.92 (13)H6B1—C6B—H6B3110
C1—P1—C21114.62 (13)H6B2—C6B—H6B3110
C11—P1—C21105.16 (12)C12—C11—C16118.0 (3)
C1—P1—C31107.56 (13)C12—C11—P1120.9 (2)
C11—P1—C31107.30 (13)C16—C11—P1121.0 (2)
C21—P1—C31110.06 (13)C11—C12—C13121.0 (3)
C1—P1—O256.31 (10)C11—C12—H12119.5
C11—P1—O2166.38 (10)C13—C12—H12119.5
C21—P1—O287.10 (10)C14—C13—C12120.1 (3)
C31—P1—O273.01 (10)C14—C13—H13119.9
C1—P1—O350.08 (10)C12—C13—H13120.0
C11—P1—O365.79 (10)C13—C14—C15119.9 (3)
C21—P1—O3109.57 (10)C13—C14—H14120.0
C31—P1—O3140.13 (11)C15—C14—H14120.0
O2—P1—O3104.87 (6)C16—C15—C14119.9 (3)
C2—O1—C4114.9 (2)C16—C15—H15120.0
C2—O1—O487.45 (17)C14—C15—H15120.0
C4—O1—O4157.52 (18)C11—C16—C15121.0 (3)
C2—O2—P169.18 (16)C11—C16—H16119.5
C3—O3—C5B109.3 (9)C15—C16—H16119.5
C3—O3—C5A116.9 (3)C26—C21—C22119.1 (3)
C3—O3—P169.21 (15)C26—C21—P1119.4 (2)
C5B—O3—P1177.3 (7)C22—C21—P1121.4 (2)
C5A—O3—P1148.7 (2)C21—C22—C23120.7 (3)
C3—O4—O181.51 (18)C21—C22—H22119.6
C2—C1—C3124.2 (3)C23—C22—H22119.6
C2—C1—P1110.9 (2)C22—C23—C24118.7 (3)
C3—C1—P1124.8 (2)C22—C23—H23120.7
O2—C2—O1120.6 (3)C24—C23—H23120.7
O2—C2—C1123.0 (3)C25—C24—C23121.2 (3)
O1—C2—C1116.4 (3)C25—C24—H24119.4
O4—C3—O3121.1 (3)C23—C24—H24119.4
O4—C3—C1127.4 (3)C24—C25—C26120.1 (3)
O3—C3—C1111.5 (2)C24—C25—H25119.9
O1—C4—H4A109.5C26—C25—H25119.9
O1—C4—H4B109.5C21—C26—C25120.2 (3)
H4A—C4—H4B109.5C21—C26—H26119.9
O1—C4—H4C109.5C25—C26—H26119.9
H4A—C4—H4C109.5C36—C31—C32119.1 (3)
H4B—C4—H4C109.5C36—C31—P1123.4 (2)
O3—C5A—C6A108.2 (4)C32—C31—P1117.5 (2)
O3—C5A—H5A1110.1C31—C32—C33119.6 (3)
C6A—C5A—H5A1110.1C31—C32—H32120.2
O3—C5A—H5A2110.1C33—C32—H32120.2
C6A—C5A—H5A2110.0C34—C33—C32120.5 (3)
H5A1—C5A—H5A2108.4C34—C33—H33119.7
O3—C5B—C6B99.3 (14)C32—C33—H33119.7
O3—C5B—H5B1111.8C35—C34—C33119.6 (3)
C6B—C5B—H5B1111.7C35—C34—H34120.2
O3—C5B—H5B2112.0C33—C34—H34120.2
C6B—C5B—H5B2112.2C34—C35—C36120.9 (3)
H5B1—C5B—H5B2109.6C34—C35—H35119.5
C5B—C6B—H6B1109.0C36—C35—H35119.5
C5B—C6B—H6B2109.0C31—C36—C35120.1 (3)
H6B1—C6B—H6B2109C31—C36—H36119.9
C5B—C6B—H6B3110C35—C36—H36119.9
P1—C1—C2—O210.2 (4)P1—C1—C3—O4154.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O4i0.932.483.376 (4)162
C25—H25···O2ii0.932.493.392 (4)162
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x+1/2, y1/2, z+1/2.
(II) dimethyl 2-(triphenylphosphoranylidene)malonate top
Crystal data top
C23H21O4PF(000) = 1648
Mr = 392.37Dx = 1.314 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6277 reflections
a = 10.1031 (8) Åθ = 2.3–26.5°
b = 14.6961 (11) ŵ = 0.17 mm1
c = 26.756 (2) ÅT = 273 K
β = 92.734 (1)°Block, colourless
V = 3968.1 (5) Å30.18 × 0.18 × 0.16 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
6466 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
Graphite monochromatorθmax = 28.1°, θmin = 1.6°
φ and ω scansh = 1313
33032 measured reflectionsk = 1919
8973 independent reflectionsl = 3433
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0708P)2 + 0.4925P]
where P = (Fo2 + 2Fc2)/3
8973 reflections(Δ/σ)max < 0.001
509 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

Experimental. 1H NMR (CDCl3, δ, p.p.m.): 3.34 (s, 6H), 7.5–8.0 (m, 15H). IR (KBr): 1716.6, 1685.9 and 1628.4 (CO) cm-1.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.61745 (5)0.36378 (3)0.213009 (19)0.03310 (14)
O10.48785 (14)0.20077 (10)0.24484 (6)0.0493 (4)
O20.28520 (15)0.25678 (12)0.25339 (9)0.0748 (6)
O30.49442 (13)0.50540 (9)0.26611 (6)0.0440 (4)
O40.28666 (13)0.45071 (11)0.26383 (6)0.0546 (4)
C10.46488 (18)0.35641 (13)0.24016 (8)0.0358 (4)
C20.4000 (2)0.27085 (14)0.24599 (8)0.0417 (5)
C40.4335 (3)0.11157 (16)0.23834 (12)0.0723 (8)
H4A0.38300.09640.26670.108*
H4B0.50410.06840.23550.108*
H4C0.37690.11000.20850.108*
C30.40225 (19)0.43837 (14)0.25703 (7)0.0386 (5)
C50.4449 (2)0.59640 (15)0.27014 (10)0.0592 (7)
H5A0.38880.61040.24120.089*
H5B0.51790.63830.27230.089*
H5C0.39500.60150.29970.089*
C110.6213 (2)0.46969 (14)0.17900 (8)0.0396 (5)
C120.5114 (2)0.49521 (16)0.14906 (9)0.0527 (6)
H120.43840.45670.14570.063*
C130.5104 (3)0.57792 (18)0.12430 (10)0.0654 (7)
H130.43750.59420.10370.079*
C140.6163 (4)0.63587 (18)0.12996 (11)0.0749 (9)
H140.61520.69140.11330.090*
C150.7231 (3)0.61196 (19)0.16006 (12)0.0762 (9)
H150.79390.65200.16450.091*
C160.7273 (2)0.52880 (16)0.18413 (10)0.0557 (6)
H160.80180.51260.20390.067*
C210.75894 (19)0.36174 (13)0.25651 (8)0.0363 (4)
C220.7401 (2)0.37376 (14)0.30691 (8)0.0435 (5)
H220.65500.38080.31810.052*
C230.8478 (2)0.37534 (16)0.34048 (9)0.0552 (6)
H230.83540.38450.37430.066*
C240.9737 (2)0.36343 (17)0.32413 (10)0.0591 (7)
H241.04590.36400.34710.071*
C250.9937 (2)0.35075 (16)0.27457 (10)0.0555 (6)
H251.07900.34230.26380.067*
C260.8873 (2)0.35046 (15)0.24052 (9)0.0488 (6)
H260.90100.34270.20670.059*
C310.64474 (19)0.27403 (14)0.16818 (8)0.0377 (5)
C320.7124 (2)0.19526 (15)0.18286 (9)0.0481 (5)
H320.74520.18900.21570.058*
C330.7310 (3)0.12633 (17)0.14887 (10)0.0603 (7)
H330.77730.07420.15890.072*
C340.6818 (2)0.13439 (18)0.10054 (10)0.0608 (7)
H340.69290.08710.07800.073*
C350.6162 (2)0.21184 (18)0.08521 (9)0.0601 (7)
H350.58380.21750.05220.072*
C360.5984 (2)0.28166 (16)0.11895 (9)0.0507 (6)
H360.55460.33440.10830.061*
P20.14040 (5)0.23867 (3)0.019001 (19)0.03339 (14)
O50.26852 (13)0.39912 (9)0.01229 (6)0.0471 (4)
O60.47910 (14)0.35080 (10)0.00490 (7)0.0549 (4)
O70.48632 (13)0.17156 (10)0.03133 (6)0.0451 (4)
O80.29961 (14)0.09048 (9)0.02638 (6)0.0472 (4)
C60.29971 (18)0.24510 (13)0.00282 (7)0.0347 (4)
C70.36227 (19)0.33301 (14)0.00618 (8)0.0382 (5)
C80.35766 (19)0.16273 (14)0.02024 (7)0.0351 (4)
C90.3135 (3)0.49158 (15)0.00870 (12)0.0702 (8)
H9A0.36950.49890.02100.105*
H9B0.23850.53150.00730.105*
H9C0.36250.50630.03750.105*
C100.5552 (2)0.09001 (15)0.04373 (9)0.0513 (6)
H10A0.57670.05610.01380.077*
H10B0.63530.10550.05970.077*
H10C0.49990.05380.06610.077*
C410.1214 (2)0.13296 (13)0.05190 (7)0.0371 (4)
C420.2244 (2)0.10326 (15)0.08454 (8)0.0468 (5)
H420.30350.13570.08710.056*
C430.2090 (3)0.02589 (15)0.11297 (9)0.0531 (6)
H430.27720.00680.13510.064*
C440.0930 (3)0.02296 (16)0.10852 (9)0.0568 (6)
H440.08290.07490.12780.068*
C450.0076 (2)0.00419 (16)0.07597 (9)0.0543 (6)
H450.08510.02980.07280.065*
C460.0057 (2)0.08215 (14)0.04764 (8)0.0435 (5)
H460.06330.10060.02570.052*
C510.01025 (19)0.25060 (13)0.02921 (8)0.0365 (4)
C520.0442 (2)0.25322 (14)0.07856 (8)0.0418 (5)
H520.13230.24640.08640.050*
C530.0517 (2)0.26588 (16)0.11641 (9)0.0520 (6)
H530.02790.26720.14950.062*
C540.1818 (2)0.27657 (16)0.10534 (10)0.0568 (6)
H540.24590.28550.13100.068*
C550.2179 (2)0.27408 (16)0.05650 (10)0.0551 (6)
H550.30630.28100.04910.066*
C560.1227 (2)0.26128 (15)0.01841 (9)0.0471 (5)
H560.14730.25980.01460.057*
C610.1127 (2)0.32753 (14)0.06472 (8)0.0386 (5)
C620.0396 (2)0.40447 (16)0.05198 (9)0.0541 (6)
H620.00130.41050.01980.065*
C630.0232 (3)0.47256 (19)0.08692 (11)0.0701 (8)
H630.02700.52380.07840.084*
C640.0807 (3)0.4644 (2)0.13388 (11)0.0704 (8)
H640.07090.51080.15700.084*
C650.1523 (3)0.3890 (2)0.14717 (10)0.0657 (7)
H650.19040.38360.17940.079*
C660.1682 (2)0.32040 (17)0.11259 (8)0.0521 (6)
H660.21690.26890.12180.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0283 (3)0.0337 (3)0.0373 (3)0.0004 (2)0.0021 (2)0.0015 (2)
O10.0384 (8)0.0368 (8)0.0732 (11)0.0006 (6)0.0053 (7)0.0083 (7)
O20.0349 (9)0.0505 (10)0.1404 (18)0.0066 (7)0.0190 (10)0.0102 (11)
O30.0344 (8)0.0384 (8)0.0595 (10)0.0022 (6)0.0044 (7)0.0087 (7)
O40.0309 (8)0.0565 (10)0.0773 (12)0.0005 (7)0.0098 (7)0.0159 (8)
C10.0276 (10)0.0372 (11)0.0425 (12)0.0019 (8)0.0022 (8)0.0006 (9)
C20.0331 (11)0.0430 (12)0.0489 (13)0.0007 (9)0.0005 (9)0.0066 (10)
C40.0665 (18)0.0385 (14)0.111 (2)0.0067 (12)0.0016 (16)0.0104 (14)
C30.0307 (10)0.0455 (12)0.0395 (11)0.0014 (9)0.0014 (9)0.0025 (9)
C50.0559 (15)0.0416 (14)0.0804 (19)0.0001 (11)0.0068 (13)0.0079 (12)
C110.0400 (11)0.0388 (12)0.0405 (12)0.0020 (9)0.0070 (9)0.0026 (9)
C120.0583 (15)0.0467 (14)0.0529 (15)0.0063 (11)0.0020 (11)0.0063 (11)
C130.086 (2)0.0529 (16)0.0576 (16)0.0204 (14)0.0003 (14)0.0127 (12)
C140.116 (3)0.0428 (15)0.0674 (19)0.0037 (16)0.0219 (18)0.0169 (13)
C150.096 (2)0.0527 (17)0.081 (2)0.0266 (15)0.0141 (18)0.0153 (15)
C160.0531 (14)0.0501 (14)0.0643 (16)0.0120 (11)0.0079 (12)0.0099 (12)
C210.0305 (10)0.0361 (11)0.0420 (12)0.0005 (8)0.0004 (8)0.0016 (9)
C220.0374 (11)0.0467 (13)0.0463 (13)0.0004 (9)0.0012 (9)0.0014 (10)
C230.0559 (15)0.0621 (16)0.0463 (14)0.0013 (12)0.0099 (11)0.0028 (11)
C240.0472 (14)0.0633 (17)0.0649 (17)0.0018 (11)0.0179 (12)0.0018 (13)
C250.0296 (11)0.0609 (16)0.0758 (18)0.0007 (10)0.0012 (11)0.0012 (13)
C260.0348 (11)0.0588 (15)0.0529 (14)0.0009 (10)0.0051 (10)0.0022 (11)
C310.0335 (10)0.0388 (11)0.0408 (12)0.0006 (8)0.0024 (9)0.0029 (9)
C320.0498 (13)0.0459 (13)0.0482 (13)0.0087 (10)0.0012 (10)0.0024 (10)
C330.0632 (16)0.0458 (14)0.0714 (18)0.0138 (12)0.0013 (13)0.0098 (12)
C340.0584 (16)0.0615 (16)0.0624 (17)0.0047 (12)0.0028 (13)0.0244 (13)
C350.0608 (15)0.0728 (18)0.0458 (14)0.0064 (13)0.0073 (11)0.0154 (13)
C360.0516 (13)0.0516 (14)0.0485 (14)0.0070 (11)0.0021 (11)0.0035 (11)
P20.0311 (3)0.0332 (3)0.0360 (3)0.0008 (2)0.0028 (2)0.0007 (2)
O50.0356 (8)0.0338 (8)0.0721 (11)0.0006 (6)0.0047 (7)0.0061 (7)
O60.0321 (8)0.0422 (9)0.0902 (13)0.0053 (6)0.0001 (8)0.0035 (8)
O70.0337 (8)0.0427 (8)0.0597 (10)0.0001 (6)0.0106 (7)0.0071 (7)
O80.0445 (9)0.0374 (8)0.0604 (10)0.0076 (7)0.0089 (7)0.0073 (7)
C60.0300 (10)0.0340 (11)0.0402 (11)0.0020 (8)0.0028 (8)0.0015 (8)
C70.0336 (11)0.0377 (11)0.0432 (12)0.0017 (9)0.0003 (9)0.0031 (9)
C80.0332 (10)0.0397 (11)0.0324 (11)0.0007 (9)0.0019 (8)0.0033 (8)
C90.0587 (16)0.0330 (13)0.120 (3)0.0014 (11)0.0099 (16)0.0009 (14)
C100.0442 (13)0.0505 (14)0.0598 (15)0.0107 (10)0.0085 (11)0.0033 (11)
C410.0388 (11)0.0366 (11)0.0364 (11)0.0004 (9)0.0072 (9)0.0011 (8)
C420.0459 (13)0.0464 (13)0.0482 (13)0.0010 (10)0.0028 (10)0.0050 (10)
C430.0684 (16)0.0454 (14)0.0455 (13)0.0115 (12)0.0030 (11)0.0055 (11)
C440.0817 (18)0.0354 (13)0.0548 (15)0.0013 (12)0.0188 (13)0.0046 (11)
C450.0605 (15)0.0421 (13)0.0615 (16)0.0126 (11)0.0165 (13)0.0022 (11)
C460.0442 (12)0.0392 (12)0.0475 (13)0.0038 (9)0.0078 (10)0.0005 (9)
C510.0341 (10)0.0327 (11)0.0425 (12)0.0007 (8)0.0009 (9)0.0016 (9)
C520.0400 (11)0.0409 (12)0.0444 (13)0.0011 (9)0.0015 (9)0.0001 (9)
C530.0604 (15)0.0509 (14)0.0438 (13)0.0018 (11)0.0068 (11)0.0021 (10)
C540.0505 (14)0.0507 (14)0.0669 (18)0.0014 (11)0.0198 (12)0.0054 (12)
C550.0349 (12)0.0493 (14)0.0806 (19)0.0008 (10)0.0030 (12)0.0063 (12)
C560.0378 (12)0.0489 (13)0.0550 (14)0.0025 (10)0.0054 (10)0.0043 (10)
C610.0371 (11)0.0395 (11)0.0397 (12)0.0027 (9)0.0060 (9)0.0033 (9)
C620.0626 (15)0.0486 (14)0.0510 (14)0.0124 (11)0.0008 (11)0.0077 (11)
C630.082 (2)0.0580 (17)0.0704 (19)0.0196 (14)0.0062 (15)0.0152 (14)
C640.0803 (19)0.0687 (19)0.0630 (18)0.0000 (15)0.0136 (15)0.0270 (15)
C650.0695 (18)0.082 (2)0.0457 (15)0.0074 (15)0.0018 (13)0.0160 (13)
C660.0526 (14)0.0580 (15)0.0454 (14)0.0031 (11)0.0011 (11)0.0056 (11)
Geometric parameters (Å, º) top
P1—C11.738 (2)P2—C61.7408 (19)
P1—C211.800 (2)P2—C411.800 (2)
P1—C111.804 (2)P2—C511.806 (2)
P1—C311.813 (2)P2—C611.820 (2)
O1—C21.361 (2)O5—C71.361 (2)
O1—C41.429 (3)O5—C91.434 (3)
O2—C21.204 (2)O6—C71.208 (2)
O3—C31.369 (2)O7—C81.353 (2)
O3—C51.434 (3)O7—C101.433 (2)
O4—C31.204 (2)O8—C81.220 (2)
C1—C21.430 (3)C6—C81.432 (3)
C1—C31.443 (3)C6—C71.443 (3)
C4—H4A0.9600C9—H9A0.9600
C4—H4B0.9600C9—H9B0.9600
C4—H4C0.9600C9—H9C0.9600
C5—H5A0.9600C10—H10A0.9600
C5—H5B0.9600C10—H10B0.9600
C5—H5C0.9600C10—H10C0.9600
C11—C161.380 (3)C41—C461.387 (3)
C11—C121.390 (3)C41—C421.396 (3)
C12—C131.384 (3)C42—C431.381 (3)
C12—H120.9300C42—H420.9300
C13—C141.370 (4)C43—C441.375 (3)
C13—H130.9300C43—H430.9300
C14—C151.361 (4)C44—C451.366 (3)
C14—H140.9300C44—H440.9300
C15—C161.381 (3)C45—C461.384 (3)
C15—H150.9300C45—H450.9300
C16—H160.9300C46—H460.9300
C21—C221.382 (3)C51—C521.380 (3)
C21—C261.394 (3)C51—C561.397 (3)
C22—C231.378 (3)C52—C531.380 (3)
C22—H220.9300C52—H520.9300
C23—C241.376 (3)C53—C541.370 (3)
C23—H230.9300C53—H530.9300
C24—C251.363 (4)C54—C551.374 (4)
C24—H240.9300C54—H540.9300
C25—C261.376 (3)C55—C561.380 (3)
C25—H250.9300C55—H550.9300
C26—H260.9300C56—H560.9300
C31—C361.382 (3)C61—C661.378 (3)
C31—C321.391 (3)C61—C621.384 (3)
C32—C331.380 (3)C62—C631.385 (3)
C32—H320.9300C62—H620.9300
C33—C341.368 (4)C63—C641.364 (4)
C33—H330.9300C63—H630.9300
C34—C351.370 (3)C64—C651.361 (4)
C34—H340.9300C64—H640.9300
C35—C361.384 (3)C65—C661.383 (3)
C35—H350.9300C65—H650.9300
C36—H360.9300C66—H660.9300
P1—O32.8396 (15)P2—O52.8355 (14)
P1—O12.8784 (15)P2—O82.9985 (15)
O2—O42.864 (2)O6—O72.729 (2)
C1—P1—C21114.92 (10)C6—P2—C41109.43 (9)
C1—P1—C11107.80 (9)C6—P2—C51114.11 (9)
C21—P1—C11107.75 (9)C41—P2—C51110.00 (9)
C1—P1—C31113.39 (9)C6—P2—C61111.15 (9)
C21—P1—C31105.93 (9)C41—P2—C61105.49 (9)
C11—P1—C31106.64 (10)C51—P2—C61106.28 (9)
C1—P1—O354.45 (7)C6—P2—O554.08 (7)
C21—P1—O392.40 (7)C41—P2—O5157.33 (8)
C11—P1—O368.94 (7)C51—P2—O592.03 (7)
C31—P1—O3161.51 (7)C61—P2—O571.87 (7)
C1—P1—O153.10 (7)C6—P2—O851.76 (7)
C21—P1—O198.81 (7)C41—P2—O869.08 (7)
C11—P1—O1152.66 (7)C51—P2—O899.65 (7)
C31—P1—O171.08 (7)C61—P2—O8153.63 (7)
O3—P1—O1104.23 (5)O5—P2—O8102.90 (4)
C2—O1—C4116.74 (17)C7—O5—C9116.86 (16)
C2—O1—P171.53 (11)C7—O5—P272.29 (10)
C4—O1—P1154.86 (16)C9—O5—P2156.28 (16)
C2—O2—O481.05 (13)C7—O6—O779.74 (12)
C3—O3—C5116.61 (16)C8—O7—C10116.94 (16)
C3—O3—P172.19 (10)C8—O7—O689.88 (11)
C5—O3—P1152.12 (14)C10—O7—O6152.44 (13)
C3—O4—O280.55 (13)C8—O8—P264.99 (11)
C2—C1—C3119.32 (17)C8—C6—C7123.32 (17)
C2—C1—P1121.38 (15)C8—C6—P2117.53 (14)
C3—C1—P1119.30 (14)C7—C6—P2118.96 (15)
O2—C2—O1120.55 (19)O6—C7—O5121.48 (18)
O2—C2—C1128.3 (2)O6—C7—C6128.49 (19)
O1—C2—C1111.10 (17)O5—C7—C6110.01 (16)
O1—C4—H4A109.5O8—C8—O7120.96 (18)
O1—C4—H4B109.5O8—C8—C6125.30 (18)
H4A—C4—H4B109.5O7—C8—C6113.71 (17)
O1—C4—H4C109.5O5—C9—H9A109.5
H4A—C4—H4C109.5O5—C9—H9B109.5
H4B—C4—H4C109.5H9A—C9—H9B109.5
O4—C3—O3121.40 (19)O5—C9—H9C109.5
O4—C3—C1128.02 (19)H9A—C9—H9C109.5
O3—C3—C1110.57 (16)H9B—C9—H9C109.5
O3—C5—H5A109.5O7—C10—H10A109.5
O3—C5—H5B109.5O7—C10—H10B109.5
H5A—C5—H5B109.5H10A—C10—H10B109.5
O3—C5—H5C109.5O7—C10—H10C109.5
H5A—C5—H5C109.5H10A—C10—H10C109.5
H5B—C5—H5C109.5H10B—C10—H10C109.5
C16—C11—C12118.8 (2)C46—C41—C42118.89 (19)
C16—C11—P1121.89 (17)C46—C41—P2122.23 (16)
C12—C11—P1119.17 (17)C42—C41—P2118.81 (16)
C13—C12—C11120.0 (2)C43—C42—C41120.1 (2)
C13—C12—H12120.0C43—C42—H42119.9
C11—C12—H12120.0C41—C42—H42119.9
C14—C13—C12120.4 (3)C44—C43—C42120.0 (2)
C14—C13—H13119.8C44—C43—H43120.0
C12—C13—H13119.8C42—C43—H43120.0
C15—C14—C13119.8 (2)C45—C44—C43120.5 (2)
C15—C14—H14120.1C45—C44—H44119.7
C13—C14—H14120.1C43—C44—H44119.7
C14—C15—C16120.7 (3)C44—C45—C46120.2 (2)
C14—C15—H15119.7C44—C45—H45119.9
C16—C15—H15119.7C46—C45—H45119.9
C11—C16—C15120.3 (2)C45—C46—C41120.3 (2)
C11—C16—H16119.9C45—C46—H46119.9
C15—C16—H16119.9C41—C46—H46119.9
C22—C21—C26119.20 (19)C52—C51—C56118.67 (19)
C22—C21—P1119.12 (15)C52—C51—P2118.71 (15)
C26—C21—P1121.66 (16)C56—C51—P2122.55 (16)
C23—C22—C21119.8 (2)C53—C52—C51120.5 (2)
C23—C22—H22120.1C53—C52—H52119.7
C21—C22—H22120.1C51—C52—H52119.7
C24—C23—C22120.3 (2)C54—C53—C52120.3 (2)
C24—C23—H23119.9C54—C53—H53119.9
C22—C23—H23119.9C52—C53—H53119.9
C25—C24—C23120.5 (2)C53—C54—C55120.2 (2)
C25—C24—H24119.7C53—C54—H54119.9
C23—C24—H24119.7C55—C54—H54119.9
C24—C25—C26119.8 (2)C54—C55—C56119.9 (2)
C24—C25—H25120.1C54—C55—H55120.0
C26—C25—H25120.1C56—C55—H55120.0
C25—C26—C21120.3 (2)C55—C56—C51120.4 (2)
C25—C26—H26119.8C55—C56—H56119.8
C21—C26—H26119.8C51—C56—H56119.8
C36—C31—C32118.5 (2)C66—C61—C62118.7 (2)
C36—C31—P1121.09 (16)C66—C61—P2120.10 (17)
C32—C31—P1120.46 (16)C62—C61—P2121.19 (17)
C33—C32—C31120.4 (2)C61—C62—C63120.2 (2)
C33—C32—H32119.8C61—C62—H62119.9
C31—C32—H32119.8C63—C62—H62119.9
C34—C33—C32120.3 (2)C64—C63—C62119.9 (3)
C34—C33—H33119.9C64—C63—H63120.0
C32—C33—H33119.9C62—C63—H63120.0
C33—C34—C35120.2 (2)C65—C64—C63120.7 (2)
C33—C34—H34119.9C65—C64—H64119.7
C35—C34—H34119.9C63—C64—H64119.7
C34—C35—C36119.8 (2)C64—C65—C66119.7 (2)
C34—C35—H35120.1C64—C65—H65120.1
C36—C35—H35120.1C66—C65—H65120.1
C31—C36—C35120.9 (2)C61—C66—C65120.8 (2)
C31—C36—H36119.6C61—C66—H66119.6
C35—C36—H36119.6C65—C66—H66119.6
P1—C1—C2—O2162.0 (2)P2—C6—C7—O6154.6 (2)
P1—C1—C3—O4158.20 (19)P2—C6—C8—O88.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C25—H25···O2i0.932.463.326 (3)155
C35—H35···O70.932.493.377 (3)159
Symmetry code: (i) x+1, y, z.
 

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