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Acta Cryst. (2009). E65, o2444    [ doi:10.1107/S160053680903356X ]

Triphenylphosphine oxide-2-(4-hydroxybenzenyl)-4,4,5,5-tetramethylimidazolidine-1-oxyl 3-oxide (1/1)

L.-L. Jing, H.-B. Wang and X.-L. Sun

Abstract top

The title compound, C18H15OP·C13H17N2O3, belongs to a series of molecular systems based on triphenylphosphine oxide. The O atom of the oxide group acts as an acceptor for hydrogen bonds from -OH groups of the nitronyl nitroxide. The crystal structure is stabilized by O-H...O hydrogen bonds.

Comment top

In the title compound, the dihedral angle between the imidazole ring of the nitronyl nitroxide part and phenyl rings is 161.2°(2). The the nitronyl nitroxide and the triphenylphosphine oxide (TPPO) are linked by an O—H···O hydrogen bond. The O atom of the oxide group acts as an acceptor for hydrogen bonds from OH groups of the nitronyl nitroxide (Table1 and Fig.2).

Related literature top

For related structures, see: Fuquen & Lechat (1992); Ng (2009). For hydrogen bonding, see: Etter (1990).

Experimental top

Crystals of the title compound (I), were obtained by slow evaporation of equimolecular quantities of 4,4,5,5-tetramethyl-2-(4-hydroxybenzenyl)-imidazolidine-1-oxyl-3-oxide (2.49 g, 10.0 mmol) and triphenylphosphine oxide (2.78 g, 10.0 mmol) in 150 ml of dry acetonitrile. After three days, dark blue crystal of a good quality suitable for X-ray analysis were obtained.

Refinement top

In both structures all the H atoms were discernible in the difference Fourier maps. However, they were constrained by riding model approximation. C—H~methyl~=0.96 Å; C—Hãryl~=0.93 Å; Uĩso~H~methyl~ and Uĩso~Hãryl~ are 1.5 U ~eq~(C) and 1.2 U ~eq ~(C), respectively.

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound (I), showing the atomic labelling scheme. The displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The packing of the title molecules (I), viewed down the a axis. Dotted lines indicate hydrogen bonds.
Triphenylphosphine oxide–2-(4-hydroxybenzenyl)-4,4,5,5-tetramethylimidazolidine-1-oxyl 3-oxide (1/1) top
Crystal data top
C18H15OP·C13H17N2O3Z = 2
Mr = 527.56F(000) = 558
Triclinic, P1Dx = 1.215 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8431 (11) ÅCell parameters from 1409 reflections
b = 12.0786 (15) Åθ = 2.4–20.6°
c = 13.9649 (16) ŵ = 0.13 mm−1
α = 86.386 (2)°T = 296 K
β = 82.724 (2)°Block, blue
γ = 77.318 (2)°0.39 × 0.28 × 0.16 mm
V = 1442.6 (3) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer		5071 independent reflections
Radiation source: fine-focus sealed tube2859 reflections with I > 2σ(I)
graphiteRint = 0.024
φ and ω scansθmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		h = −10→10
Tmin = 0.951, Tmax = 0.979k = −9→14
7342 measured reflectionsl = −16→16
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.124 w = 1/[σ2(Fo2) + (0.05P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
5071 reflectionsΔρmax = 0.20 e Å−3
349 parametersΔρmin = −0.27 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0101 (15)
Crystal data top
C18H15OP·C13H17N2O3γ = 77.318 (2)°
Mr = 527.56V = 1442.6 (3) Å3
Triclinic, P1Z = 2
a = 8.8431 (11) ÅMo Kα radiation
b = 12.0786 (15) ŵ = 0.13 mm−1
c = 13.9649 (16) ÅT = 296 K
α = 86.386 (2)°0.39 × 0.28 × 0.16 mm
β = 82.724 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		5071 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)		2859 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.979Rint = 0.024
7342 measured reflectionsθmax = 25.1°
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.124Δρmax = 0.20 e Å−3
S = 1.08Δρmin = −0.27 e Å−3
5071 reflectionsAbsolute structure: ?
349 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

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) top
xyzUiso*/Ueq
P10.27687 (7)0.23526 (6)0.58436 (4)0.0520 (2)
N10.4223 (2)0.70728 (19)1.07295 (14)0.0624 (6)
N20.2585 (2)0.69871 (16)0.97237 (13)0.0507 (5)
O10.20487 (18)0.22532 (16)0.49552 (11)0.0670 (5)
O20.1903 (2)0.70493 (15)0.89585 (12)0.0675 (5)
O30.5469 (2)0.7152 (2)1.10822 (12)0.0932 (7)
O40.8088 (2)0.85274 (18)0.67430 (11)0.0769 (6)
H40.79390.83130.62240.115*
C10.1934 (3)0.3690 (2)0.63862 (15)0.0493 (6)
C20.0567 (3)0.4339 (2)0.61134 (17)0.0613 (7)
H20.00790.40840.56450.074*
C3−0.0097 (3)0.5378 (3)0.6534 (2)0.0743 (8)
H3−0.10170.58180.63420.089*
C40.0613 (4)0.5744 (3)0.7230 (2)0.0768 (9)
H4A0.01710.64350.75130.092*
C50.1963 (4)0.5105 (3)0.75137 (19)0.0719 (8)
H50.24360.53600.79900.086*
C60.2624 (3)0.4091 (2)0.70998 (17)0.0599 (7)
H60.35480.36610.72970.072*
C70.4827 (3)0.2292 (2)0.56119 (16)0.0536 (6)
C80.5343 (3)0.3206 (3)0.51288 (19)0.0714 (8)
H80.46160.38490.49640.086*
C90.6909 (4)0.3179 (3)0.4889 (2)0.0862 (9)
H90.72340.37990.45680.103*
C100.7987 (3)0.2232 (3)0.5126 (2)0.0855 (10)
H100.90450.22110.49600.103*
C110.7519 (3)0.1319 (3)0.5605 (2)0.0829 (9)
H110.82560.06830.57700.099*
C120.5937 (3)0.1347 (2)0.58417 (19)0.0670 (8)
H120.56210.07210.61590.080*
C130.2463 (3)0.1266 (2)0.67313 (18)0.0531 (6)
C140.2980 (3)0.1184 (2)0.76328 (19)0.0669 (7)
H140.35490.16950.77900.080*
C150.2659 (4)0.0350 (3)0.8302 (2)0.0864 (9)
H150.30170.02960.89050.104*
C160.1810 (4)−0.0395 (3)0.8072 (3)0.0989 (11)
H160.1578−0.09470.85260.119*
C170.1304 (4)−0.0339 (3)0.7190 (3)0.0978 (11)
H170.0738−0.08550.70380.117*
C180.1636 (3)0.0491 (2)0.6520 (2)0.0737 (8)
H180.12930.05260.59140.088*
C190.2785 (3)0.6952 (3)1.13670 (18)0.0708 (8)
C200.3193 (4)0.6162 (4)1.2228 (2)0.1369 (17)
H20A0.38290.54541.20060.205*
H20B0.22520.60281.25950.205*
H20C0.37570.65041.26290.205*
C210.2011 (4)0.8149 (3)1.1698 (2)0.1209 (14)
H21A0.27170.84391.20330.181*
H21B0.10770.81231.21230.181*
H21C0.17550.86361.11450.181*
C220.1890 (3)0.6513 (2)1.06455 (17)0.0610 (7)
C230.0150 (3)0.6928 (3)1.0780 (2)0.0964 (11)
H23A−0.00980.77441.07520.145*
H23B−0.02660.66571.13970.145*
H23C−0.02990.66501.02780.145*
C240.2295 (4)0.5222 (2)1.0561 (2)0.0959 (10)
H24A0.18190.50201.00350.144*
H24B0.19120.48711.11510.144*
H24C0.34070.49661.04430.144*
C250.4003 (3)0.7204 (2)0.97831 (16)0.0496 (6)
C260.5070 (3)0.7532 (2)0.89941 (16)0.0490 (6)
C270.4924 (3)0.7343 (2)0.80365 (16)0.0575 (7)
H270.41420.69900.79060.069*
C280.5908 (3)0.7666 (2)0.72880 (17)0.0610 (7)
H280.57830.75320.66570.073*
C290.7083 (3)0.8187 (2)0.74579 (17)0.0574 (7)
C300.7242 (3)0.8376 (3)0.84031 (18)0.0766 (9)
H300.80220.87340.85300.092*
C310.6268 (3)0.8044 (2)0.91523 (18)0.0717 (8)
H310.64130.81640.97830.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0468 (4)0.0631 (5)0.0482 (4)−0.0173 (3)−0.0024 (3)−0.0048 (3)
N10.0557 (14)0.0884 (18)0.0443 (13)−0.0201 (12)−0.0038 (10)−0.0002 (11)
N20.0525 (12)0.0515 (13)0.0485 (12)−0.0131 (10)−0.0037 (10)−0.0021 (10)
O10.0613 (11)0.0943 (14)0.0500 (10)−0.0218 (10)−0.0099 (8)−0.0124 (9)
O20.0683 (12)0.0825 (14)0.0614 (11)−0.0342 (10)−0.0140 (9)0.0011 (10)
O30.0759 (13)0.161 (2)0.0569 (11)−0.0530 (14)−0.0201 (10)0.0121 (12)
O40.0873 (13)0.1037 (16)0.0526 (10)−0.0559 (12)0.0090 (10)−0.0096 (11)
C10.0469 (14)0.0569 (16)0.0454 (14)−0.0163 (13)−0.0044 (11)0.0051 (12)
C20.0529 (16)0.070 (2)0.0592 (16)−0.0133 (15)−0.0035 (13)0.0022 (15)
C30.0604 (18)0.066 (2)0.084 (2)0.0040 (16)0.0045 (16)0.0036 (18)
C40.091 (2)0.060 (2)0.070 (2)−0.0119 (19)0.0190 (17)−0.0071 (16)
C50.093 (2)0.065 (2)0.0616 (18)−0.0270 (19)−0.0041 (16)−0.0083 (16)
C60.0645 (17)0.0560 (18)0.0608 (16)−0.0154 (14)−0.0100 (13)−0.0002 (14)
C70.0500 (15)0.0627 (18)0.0499 (14)−0.0185 (14)0.0002 (11)−0.0040 (13)
C80.0596 (18)0.077 (2)0.0799 (19)−0.0239 (16)−0.0042 (15)0.0080 (16)
C90.070 (2)0.097 (3)0.097 (2)−0.044 (2)0.0083 (18)0.004 (2)
C100.0465 (17)0.112 (3)0.095 (2)−0.020 (2)0.0190 (16)−0.024 (2)
C110.0493 (17)0.091 (2)0.102 (2)−0.0083 (17)0.0054 (16)−0.012 (2)
C120.0500 (16)0.0664 (19)0.0819 (19)−0.0117 (15)0.0070 (14)−0.0144 (15)
C130.0438 (14)0.0548 (17)0.0609 (16)−0.0131 (13)0.0007 (12)−0.0076 (13)
C140.0778 (19)0.0577 (18)0.0661 (18)−0.0191 (15)−0.0042 (15)0.0006 (15)
C150.098 (2)0.073 (2)0.079 (2)−0.009 (2)−0.0025 (18)0.0178 (18)
C160.085 (2)0.060 (2)0.140 (3)−0.0107 (19)0.010 (2)0.028 (2)
C170.077 (2)0.063 (2)0.157 (3)−0.0315 (19)−0.003 (2)0.003 (2)
C180.0634 (18)0.0632 (19)0.099 (2)−0.0237 (16)−0.0069 (16)−0.0053 (18)
C190.0637 (18)0.097 (2)0.0549 (16)−0.0298 (17)0.0048 (14)−0.0028 (17)
C200.113 (3)0.248 (5)0.064 (2)−0.083 (3)−0.0166 (19)0.057 (3)
C210.111 (3)0.144 (4)0.114 (3)−0.040 (3)0.016 (2)−0.070 (3)
C220.0602 (17)0.070 (2)0.0546 (15)−0.0230 (15)0.0022 (13)0.0020 (14)
C230.066 (2)0.136 (3)0.091 (2)−0.037 (2)0.0027 (17)−0.001 (2)
C240.124 (3)0.062 (2)0.097 (2)−0.032 (2)0.0199 (19)0.0065 (18)
C250.0493 (15)0.0511 (16)0.0490 (15)−0.0122 (12)−0.0052 (12)−0.0025 (12)
C260.0518 (15)0.0522 (16)0.0437 (14)−0.0123 (12)−0.0048 (11)−0.0040 (12)
C270.0536 (15)0.0720 (19)0.0519 (15)−0.0253 (14)−0.0010 (12)−0.0078 (14)
C280.0647 (17)0.077 (2)0.0461 (14)−0.0242 (15)−0.0061 (13)−0.0073 (13)
C290.0635 (16)0.0638 (18)0.0488 (15)−0.0272 (14)0.0025 (13)−0.0025 (13)
C300.083 (2)0.106 (3)0.0577 (17)−0.0584 (19)0.0008 (15)−0.0151 (16)
C310.0812 (19)0.101 (2)0.0472 (15)−0.0495 (18)−0.0052 (14)−0.0092 (15)
Geometric parameters (Å, °) top
P1—O11.4871 (15)C14—H140.9300
P1—C131.789 (3)C15—C161.368 (4)
P1—C71.794 (2)C15—H150.9300
P1—C11.794 (2)C16—C171.355 (4)
N1—O31.287 (2)C16—H160.9300
N1—C251.355 (3)C17—C181.382 (4)
N1—C191.486 (3)C17—H170.9300
N2—O21.282 (2)C18—H180.9300
N2—C251.349 (3)C19—C201.517 (4)
N2—C221.491 (3)C19—C211.530 (4)
O4—C291.356 (3)C19—C221.542 (3)
O4—H40.8200C20—H20A0.9600
C1—C21.373 (3)C20—H20B0.9600
C1—C61.394 (3)C20—H20C0.9600
C2—C31.395 (3)C21—H21A0.9600
C2—H20.9300C21—H21B0.9600
C3—C41.366 (4)C21—H21C0.9600
C3—H30.9300C22—C231.502 (3)
C4—C51.362 (4)C22—C241.529 (4)
C4—H4A0.9300C23—H23A0.9600
C5—C61.366 (3)C23—H23B0.9600
C5—H50.9300C23—H23C0.9600
C6—H60.9300C24—H24A0.9600
C7—C121.382 (3)C24—H24B0.9600
C7—C81.390 (4)C24—H24C0.9600
C8—C91.377 (4)C25—C261.452 (3)
C8—H80.9300C26—C311.384 (3)
C9—C101.370 (4)C26—C271.397 (3)
C9—H90.9300C27—C281.367 (3)
C10—C111.369 (4)C27—H270.9300
C10—H100.9300C28—C291.379 (3)
C11—C121.390 (3)C28—H280.9300
C11—H110.9300C29—C301.383 (3)
C12—H120.9300C30—C311.367 (3)
C13—C181.374 (3)C30—H300.9300
C13—C141.383 (3)C31—H310.9300
C14—C151.381 (4)
O1—P1—C13111.66 (11)C16—C17—H17120.3
O1—P1—C7112.90 (10)C18—C17—H17120.3
C13—P1—C7108.14 (12)C13—C18—C17121.3 (3)
O1—P1—C1110.81 (11)C13—C18—H18119.4
C13—P1—C1107.11 (11)C17—C18—H18119.4
C7—P1—C1105.88 (11)N1—C19—C20110.5 (2)
O3—N1—C25125.7 (2)N1—C19—C21105.7 (2)
O3—N1—C19121.27 (19)C20—C19—C21110.5 (3)
C25—N1—C19112.7 (2)N1—C19—C22100.37 (19)
O2—N2—C25126.60 (19)C20—C19—C22115.7 (3)
O2—N2—C22119.92 (19)C21—C19—C22113.2 (2)
C25—N2—C22113.11 (19)C19—C20—H20A109.5
C29—O4—H4109.5C19—C20—H20B109.5
C2—C1—C6118.3 (2)H20A—C20—H20B109.5
C2—C1—P1120.01 (19)C19—C20—H20C109.5
C6—C1—P1121.70 (19)H20A—C20—H20C109.5
C1—C2—C3120.5 (2)H20B—C20—H20C109.5
C1—C2—H2119.8C19—C21—H21A109.5
C3—C2—H2119.8C19—C21—H21B109.5
C4—C3—C2119.6 (3)H21A—C21—H21B109.5
C4—C3—H3120.2C19—C21—H21C109.5
C2—C3—H3120.2H21A—C21—H21C109.5
C5—C4—C3120.5 (3)H21B—C21—H21C109.5
C5—C4—H4A119.7N2—C22—C23110.8 (2)
C3—C4—H4A119.7N2—C22—C24106.1 (2)
C4—C5—C6120.1 (3)C23—C22—C24109.8 (3)
C4—C5—H5119.9N2—C22—C1999.84 (19)
C6—C5—H5119.9C23—C22—C19115.4 (2)
C5—C6—C1120.9 (3)C24—C22—C19114.1 (2)
C5—C6—H6119.5C22—C23—H23A109.5
C1—C6—H6119.5C22—C23—H23B109.5
C12—C7—C8117.9 (2)H23A—C23—H23B109.5
C12—C7—P1123.0 (2)C22—C23—H23C109.5
C8—C7—P1119.0 (2)H23A—C23—H23C109.5
C9—C8—C7121.3 (3)H23B—C23—H23C109.5
C9—C8—H8119.4C22—C24—H24A109.5
C7—C8—H8119.4C22—C24—H24B109.5
C10—C9—C8119.7 (3)H24A—C24—H24B109.5
C10—C9—H9120.2C22—C24—H24C109.5
C8—C9—H9120.2H24A—C24—H24C109.5
C11—C10—C9120.5 (3)H24B—C24—H24C109.5
C11—C10—H10119.7N2—C25—N1106.3 (2)
C9—C10—H10119.7N2—C25—C26127.0 (2)
C10—C11—C12119.7 (3)N1—C25—C26126.7 (2)
C10—C11—H11120.2C31—C26—C27117.1 (2)
C12—C11—H11120.2C31—C26—C25121.9 (2)
C7—C12—C11120.9 (3)C27—C26—C25121.0 (2)
C7—C12—H12119.5C28—C27—C26121.4 (2)
C11—C12—H12119.5C28—C27—H27119.3
C18—C13—C14118.2 (3)C26—C27—H27119.3
C18—C13—P1118.5 (2)C27—C28—C29120.7 (2)
C14—C13—P1123.3 (2)C27—C28—H28119.6
C15—C14—C13120.7 (3)C29—C28—H28119.6
C15—C14—H14119.7O4—C29—C28123.2 (2)
C13—C14—H14119.7O4—C29—C30118.4 (2)
C16—C15—C14119.5 (3)C28—C29—C30118.4 (2)
C16—C15—H15120.2C31—C30—C29120.8 (2)
C14—C15—H15120.2C31—C30—H30119.6
C17—C16—C15120.9 (3)C29—C30—H30119.6
C17—C16—H16119.5C30—C31—C26121.5 (2)
C15—C16—H16119.5C30—C31—H31119.3
C16—C17—C18119.4 (3)C26—C31—H31119.3
O1—P1—C1—C215.0 (2)C25—N1—C19—C20146.4 (3)
C13—P1—C1—C2−107.0 (2)O3—N1—C19—C2179.6 (3)
C7—P1—C1—C2137.75 (19)C25—N1—C19—C21−94.1 (3)
O1—P1—C1—C6−166.18 (18)O3—N1—C19—C22−162.5 (2)
C13—P1—C1—C671.8 (2)C25—N1—C19—C2223.8 (3)
C7—P1—C1—C6−43.4 (2)O2—N2—C22—C23−41.3 (3)
C6—C1—C2—C30.8 (4)C25—N2—C22—C23145.2 (2)
P1—C1—C2—C3179.67 (19)O2—N2—C22—C2477.9 (3)
C1—C2—C3—C4−0.7 (4)C25—N2—C22—C24−95.6 (2)
C2—C3—C4—C50.2 (4)O2—N2—C22—C19−163.3 (2)
C3—C4—C5—C60.3 (4)C25—N2—C22—C1923.1 (3)
C4—C5—C6—C1−0.2 (4)N1—C19—C22—N2−25.6 (2)
C2—C1—C6—C5−0.4 (4)C20—C19—C22—N2−144.4 (2)
P1—C1—C6—C5−179.20 (19)C21—C19—C22—N286.6 (3)
O1—P1—C7—C12−105.0 (2)N1—C19—C22—C23−144.3 (2)
C13—P1—C7—C1219.1 (2)C20—C19—C22—C2396.8 (3)
C1—P1—C7—C12133.6 (2)C21—C19—C22—C23−32.1 (3)
O1—P1—C7—C871.1 (2)N1—C19—C22—C2487.1 (3)
C13—P1—C7—C8−164.8 (2)C20—C19—C22—C24−31.7 (3)
C1—P1—C7—C8−50.3 (2)C21—C19—C22—C24−160.7 (2)
C12—C7—C8—C9−0.3 (4)O2—N2—C25—N1177.7 (2)
P1—C7—C8—C9−176.6 (2)C22—N2—C25—N1−9.2 (3)
C7—C8—C9—C100.3 (5)O2—N2—C25—C26−1.2 (4)
C8—C9—C10—C11−0.5 (5)C22—N2—C25—C26171.8 (2)
C9—C10—C11—C120.8 (5)O3—N1—C25—N2176.5 (2)
C8—C7—C12—C110.6 (4)C19—N1—C25—N2−10.1 (3)
P1—C7—C12—C11176.8 (2)O3—N1—C25—C26−4.5 (4)
C10—C11—C12—C7−0.9 (4)C19—N1—C25—C26168.8 (2)
O1—P1—C13—C18−0.2 (2)N2—C25—C26—C31161.1 (2)
C7—P1—C13—C18−125.0 (2)N1—C25—C26—C31−17.7 (4)
C1—P1—C13—C18121.3 (2)N2—C25—C26—C27−18.9 (4)
O1—P1—C13—C14−178.3 (2)N1—C25—C26—C27162.4 (2)
C7—P1—C13—C1456.9 (2)C31—C26—C27—C28−1.0 (4)
C1—P1—C13—C14−56.8 (2)C25—C26—C27—C28178.9 (2)
C18—C13—C14—C15−0.5 (4)C26—C27—C28—C290.2 (4)
P1—C13—C14—C15177.6 (2)C27—C28—C29—O4−179.8 (2)
C13—C14—C15—C16−0.5 (4)C27—C28—C29—C300.0 (4)
C14—C15—C16—C171.2 (5)O4—C29—C30—C31−179.5 (3)
C15—C16—C17—C18−0.7 (5)C28—C29—C30—C310.6 (4)
C14—C13—C18—C171.0 (4)C29—C30—C31—C26−1.5 (5)
P1—C13—C18—C17−177.2 (2)C27—C26—C31—C301.6 (4)
C16—C17—C18—C13−0.4 (5)C25—C26—C31—C30−178.3 (3)
O3—N1—C19—C20−39.9 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O1i0.821.822.633 (2)171
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O1i0.821.822.633 (2)171
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

We thank the Natural Science Foundation of China (grant No. 20802092) for financial support.

references
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