organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aDepartment of Chemistry, School of Pharmacy, Fourth Military Medical University, Changle West Road 17, 710032 Xi-An, People's Republic of China
*Correspondence e-mail: lisydcn@yahoo.com.cn

(Received 20 July 2009; accepted 23 August 2009; online 12 September 2009)

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.

Related literature

For related structures, see: Fuquen & Lechat (1992[Fuquen, R. M. & Lechat, J. R. (1992). Acta Cryst. C48, 1690-1692.]); Ng (2009[Ng, S. W. (2009). Acta Cryst. E65, o1431.]). For hydrogen bonding, see: Etter (1990[Etter, M. (1990). Acc. Chem. Res. 23, 120-126.]).

[Scheme 1]

Experimental

Crystal data
  • C18H15OP·C13H17N2O3

  • Mr = 527.56

  • Triclinic, [P \overline 1]

  • a = 8.8431 (11) Å

  • b = 12.0786 (15) Å

  • c = 13.9649 (16) Å

  • α = 86.386 (2)°

  • β = 82.724 (2)°

  • γ = 77.318 (2)°

  • V = 1442.6 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 296 K

  • 0.39 × 0.28 × 0.16 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.951, Tmax = 0.979

  • 7342 measured reflections

  • 5071 independent reflections

  • 2859 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.124

  • S = 1.08

  • 5071 reflections

  • 349 parameters

  • Hydrogen-atom parameters constrained

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O4—H4⋯O1i 0.82 1.82 2.633 (2) 171
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2000[Bruker (2000). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


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. CH~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 m3
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 mm1
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)
Graphite monochromatorRint = 0.024
ϕ and ω scansθmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1010
Tmin = 0.951, Tmax = 0.979k = 914
7342 measured reflectionsl = 1616
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 Å3
349 parametersΔρmin = 0.27 e Å3
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 mm1
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 reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.124H-atom parameters constrained
S = 1.08Δρmax = 0.20 e Å3
5071 reflectionsΔρmin = 0.27 e Å3
349 parameters
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*
C30.0097 (3)0.5378 (3)0.6534 (2)0.0743 (8)
H30.10170.58180.63420.089*
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)
H160.15780.09470.85260.119*
C170.1304 (4)0.0339 (3)0.7190 (3)0.0978 (11)
H170.07380.08550.70380.117*
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)
H23A0.00980.77441.07520.145*
H23B0.02660.66571.13970.145*
H23C0.02990.66501.02780.145*
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, º) 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—C2107.0 (2)O3—N1—C19—C2179.6 (3)
C7—P1—C1—C2137.75 (19)C25—N1—C19—C2194.1 (3)
O1—P1—C1—C6166.18 (18)O3—N1—C19—C22162.5 (2)
C13—P1—C1—C671.8 (2)C25—N1—C19—C2223.8 (3)
C7—P1—C1—C643.4 (2)O2—N2—C22—C2341.3 (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—C40.7 (4)C25—N2—C22—C2495.6 (2)
C2—C3—C4—C50.2 (4)O2—N2—C22—C19163.3 (2)
C3—C4—C5—C60.3 (4)C25—N2—C22—C1923.1 (3)
C4—C5—C6—C10.2 (4)N1—C19—C22—N225.6 (2)
C2—C1—C6—C50.4 (4)C20—C19—C22—N2144.4 (2)
P1—C1—C6—C5179.20 (19)C21—C19—C22—N286.6 (3)
O1—P1—C7—C12105.0 (2)N1—C19—C22—C23144.3 (2)
C13—P1—C7—C1219.1 (2)C20—C19—C22—C2396.8 (3)
C1—P1—C7—C12133.6 (2)C21—C19—C22—C2332.1 (3)
O1—P1—C7—C871.1 (2)N1—C19—C22—C2487.1 (3)
C13—P1—C7—C8164.8 (2)C20—C19—C22—C2431.7 (3)
C1—P1—C7—C850.3 (2)C21—C19—C22—C24160.7 (2)
C12—C7—C8—C90.3 (4)O2—N2—C25—N1177.7 (2)
P1—C7—C8—C9176.6 (2)C22—N2—C25—N19.2 (3)
C7—C8—C9—C100.3 (5)O2—N2—C25—C261.2 (4)
C8—C9—C10—C110.5 (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—N210.1 (3)
P1—C7—C12—C11176.8 (2)O3—N1—C25—C264.5 (4)
C10—C11—C12—C70.9 (4)C19—N1—C25—C26168.8 (2)
O1—P1—C13—C180.2 (2)N2—C25—C26—C31161.1 (2)
C7—P1—C13—C18125.0 (2)N1—C25—C26—C3117.7 (4)
C1—P1—C13—C18121.3 (2)N2—C25—C26—C2718.9 (4)
O1—P1—C13—C14178.3 (2)N1—C25—C26—C27162.4 (2)
C7—P1—C13—C1456.9 (2)C31—C26—C27—C281.0 (4)
C1—P1—C13—C1456.8 (2)C25—C26—C27—C28178.9 (2)
C18—C13—C14—C150.5 (4)C26—C27—C28—C290.2 (4)
P1—C13—C14—C15177.6 (2)C27—C28—C29—O4179.8 (2)
C13—C14—C15—C160.5 (4)C27—C28—C29—C300.0 (4)
C14—C15—C16—C171.2 (5)O4—C29—C30—C31179.5 (3)
C15—C16—C17—C180.7 (5)C28—C29—C30—C310.6 (4)
C14—C13—C18—C171.0 (4)C29—C30—C31—C261.5 (5)
P1—C13—C18—C17177.2 (2)C27—C26—C31—C301.6 (4)
C16—C17—C18—C130.4 (5)C25—C26—C31—C30178.3 (3)
O3—N1—C19—C2039.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O1i0.821.822.633 (2)171
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC18H15OP·C13H17N2O3
Mr527.56
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)8.8431 (11), 12.0786 (15), 13.9649 (16)
α, β, γ (°)86.386 (2), 82.724 (2), 77.318 (2)
V3)1442.6 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.39 × 0.28 × 0.16
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.951, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
7342, 5071, 2859
Rint0.024
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.124, 1.08
No. of reflections5071
No. of parameters349
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.27

Computer programs: APEX2 (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O1i0.8201.8212.633 (2)171.00
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

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

References

First citationBruker (2000). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationEtter, M. (1990). Acc. Chem. Res. 23, 120–126.  CrossRef CAS Web of Science Google Scholar
First citationFuquen, R. M. & Lechat, J. R. (1992). Acta Cryst. C48, 1690–1692.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationNg, S. W. (2009). Acta Cryst. E65, o1431.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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