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

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

doi:10.1107/S160053680903356X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2444

doi:10.1107/S160053680903356X

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

Lin-Lin Jing,^a Hai-Bo Wang ^a and Xiao-Li Sun ^a ^*

^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 ); Ng (2009 ). For hydrogen bonding, see: Etter (1990 ).

Experimental

Crystal data

C₁₈H₁₅OP·C₁₃H₁₇N₂O₃
M_r = 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 ) T_min = 0.951, T_max = 0.979
7342 measured reflections
5071 independent reflections
2859 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.124
S = 1.08
5071 reflections
349 parameters
Hydrogen-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903356X/pb2003sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680903356X/pb2003Isup2.hkl

checkCIF report

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.

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

	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.
	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·C₁₃H₁₇N₂O₃	Z = 2
M_r = 527.56	F(000) = 558
Triclinic, P1	D_x = 1.215 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8431 (11) Å	Cell parameters from 1409 reflections
b = 12.0786 (15) Å	θ = 2.4–20.6°
c = 13.9649 (16) Å	µ = 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 tube	2859 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
T_min = 0.951, T_max = 0.979	k = −9→14
7342 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.124	w = 1/[σ²(F_o²) + (0.05P)²] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
5071 reflections	Δρ_max = 0.20 e Å⁻³
349 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0101 (15)

Crystal data top

C₁₈H₁₅OP·C₁₃H₁₇N₂O₃	γ = 77.318 (2)°
M_r = 527.56	V = 1442.6 (3) Å³
Triclinic, P1	Z = 2
a = 8.8431 (11) Å	Mo Kα radiation
b = 12.0786 (15) Å	µ = 0.13 mm⁻¹
c = 13.9649 (16) Å	T = 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)
T_min = 0.951, T_max = 0.979	R_int = 0.024
7342 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.08	Δρ_max = 0.20 e Å⁻³
5071 reflections	Δρ_min = −0.27 e Å⁻³
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

	x	y	z	U_iso*/U_eq
P1	0.27687 (7)	0.23526 (6)	0.58436 (4)	0.0520 (2)
N1	0.4223 (2)	0.70728 (19)	1.07295 (14)	0.0624 (6)
N2	0.2585 (2)	0.69871 (16)	0.97237 (13)	0.0507 (5)
O1	0.20487 (18)	0.22532 (16)	0.49552 (11)	0.0670 (5)
O2	0.1903 (2)	0.70493 (15)	0.89585 (12)	0.0675 (5)
O3	0.5469 (2)	0.7152 (2)	1.10822 (12)	0.0932 (7)
O4	0.8088 (2)	0.85274 (18)	0.67430 (11)	0.0769 (6)
H4	0.7939	0.8313	0.6224	0.115*
C1	0.1934 (3)	0.3690 (2)	0.63862 (15)	0.0493 (6)
C2	0.0567 (3)	0.4339 (2)	0.61134 (17)	0.0613 (7)
H2	0.0079	0.4084	0.5645	0.074*
C3	−0.0097 (3)	0.5378 (3)	0.6534 (2)	0.0743 (8)
H3	−0.1017	0.5818	0.6342	0.089*
C4	0.0613 (4)	0.5744 (3)	0.7230 (2)	0.0768 (9)
H4A	0.0171	0.6435	0.7513	0.092*
C5	0.1963 (4)	0.5105 (3)	0.75137 (19)	0.0719 (8)
H5	0.2436	0.5360	0.7990	0.086*
C6	0.2624 (3)	0.4091 (2)	0.70998 (17)	0.0599 (7)
H6	0.3548	0.3661	0.7297	0.072*
C7	0.4827 (3)	0.2292 (2)	0.56119 (16)	0.0536 (6)
C8	0.5343 (3)	0.3206 (3)	0.51288 (19)	0.0714 (8)
H8	0.4616	0.3849	0.4964	0.086*
C9	0.6909 (4)	0.3179 (3)	0.4889 (2)	0.0862 (9)
H9	0.7234	0.3799	0.4568	0.103*
C10	0.7987 (3)	0.2232 (3)	0.5126 (2)	0.0855 (10)
H10	0.9045	0.2211	0.4960	0.103*
C11	0.7519 (3)	0.1319 (3)	0.5605 (2)	0.0829 (9)
H11	0.8256	0.0683	0.5770	0.099*
C12	0.5937 (3)	0.1347 (2)	0.58417 (19)	0.0670 (8)
H12	0.5621	0.0721	0.6159	0.080*
C13	0.2463 (3)	0.1266 (2)	0.67313 (18)	0.0531 (6)
C14	0.2980 (3)	0.1184 (2)	0.76328 (19)	0.0669 (7)
H14	0.3549	0.1695	0.7790	0.080*
C15	0.2659 (4)	0.0350 (3)	0.8302 (2)	0.0864 (9)
H15	0.3017	0.0296	0.8905	0.104*
C16	0.1810 (4)	−0.0395 (3)	0.8072 (3)	0.0989 (11)
H16	0.1578	−0.0947	0.8526	0.119*
C17	0.1304 (4)	−0.0339 (3)	0.7190 (3)	0.0978 (11)
H17	0.0738	−0.0855	0.7038	0.117*
C18	0.1636 (3)	0.0491 (2)	0.6520 (2)	0.0737 (8)
H18	0.1293	0.0526	0.5914	0.088*
C19	0.2785 (3)	0.6952 (3)	1.13670 (18)	0.0708 (8)
C20	0.3193 (4)	0.6162 (4)	1.2228 (2)	0.1369 (17)
H20A	0.3829	0.5454	1.2006	0.205*
H20B	0.2252	0.6028	1.2595	0.205*
H20C	0.3757	0.6504	1.2629	0.205*
C21	0.2011 (4)	0.8149 (3)	1.1698 (2)	0.1209 (14)
H21A	0.2717	0.8439	1.2033	0.181*
H21B	0.1077	0.8123	1.2123	0.181*
H21C	0.1755	0.8636	1.1145	0.181*
C22	0.1890 (3)	0.6513 (2)	1.06455 (17)	0.0610 (7)
C23	0.0150 (3)	0.6928 (3)	1.0780 (2)	0.0964 (11)
H23A	−0.0098	0.7744	1.0752	0.145*
H23B	−0.0266	0.6657	1.1397	0.145*
H23C	−0.0299	0.6650	1.0278	0.145*
C24	0.2295 (4)	0.5222 (2)	1.0561 (2)	0.0959 (10)
H24A	0.1819	0.5020	1.0035	0.144*
H24B	0.1912	0.4871	1.1151	0.144*
H24C	0.3407	0.4966	1.0443	0.144*
C25	0.4003 (3)	0.7204 (2)	0.97831 (16)	0.0496 (6)
C26	0.5070 (3)	0.7532 (2)	0.89941 (16)	0.0490 (6)
C27	0.4924 (3)	0.7343 (2)	0.80365 (16)	0.0575 (7)
H27	0.4142	0.6990	0.7906	0.069*
C28	0.5908 (3)	0.7666 (2)	0.72880 (17)	0.0610 (7)
H28	0.5783	0.7532	0.6657	0.073*
C29	0.7083 (3)	0.8187 (2)	0.74579 (17)	0.0574 (7)
C30	0.7242 (3)	0.8376 (3)	0.84031 (18)	0.0766 (9)
H30	0.8022	0.8734	0.8530	0.092*
C31	0.6268 (3)	0.8044 (2)	0.91523 (18)	0.0717 (8)
H31	0.6413	0.8164	0.9783	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0468 (4)	0.0631 (5)	0.0482 (4)	−0.0173 (3)	−0.0024 (3)	−0.0048 (3)
N1	0.0557 (14)	0.0884 (18)	0.0443 (13)	−0.0201 (12)	−0.0038 (10)	−0.0002 (11)
N2	0.0525 (12)	0.0515 (13)	0.0485 (12)	−0.0131 (10)	−0.0037 (10)	−0.0021 (10)
O1	0.0613 (11)	0.0943 (14)	0.0500 (10)	−0.0218 (10)	−0.0099 (8)	−0.0124 (9)
O2	0.0683 (12)	0.0825 (14)	0.0614 (11)	−0.0342 (10)	−0.0140 (9)	0.0011 (10)
O3	0.0759 (13)	0.161 (2)	0.0569 (11)	−0.0530 (14)	−0.0201 (10)	0.0121 (12)
O4	0.0873 (13)	0.1037 (16)	0.0526 (10)	−0.0559 (12)	0.0090 (10)	−0.0096 (11)
C1	0.0469 (14)	0.0569 (16)	0.0454 (14)	−0.0163 (13)	−0.0044 (11)	0.0051 (12)
C2	0.0529 (16)	0.070 (2)	0.0592 (16)	−0.0133 (15)	−0.0035 (13)	0.0022 (15)
C3	0.0604 (18)	0.066 (2)	0.084 (2)	0.0040 (16)	0.0045 (16)	0.0036 (18)
C4	0.091 (2)	0.060 (2)	0.070 (2)	−0.0119 (19)	0.0190 (17)	−0.0071 (16)
C5	0.093 (2)	0.065 (2)	0.0616 (18)	−0.0270 (19)	−0.0041 (16)	−0.0083 (16)
C6	0.0645 (17)	0.0560 (18)	0.0608 (16)	−0.0154 (14)	−0.0100 (13)	−0.0002 (14)
C7	0.0500 (15)	0.0627 (18)	0.0499 (14)	−0.0185 (14)	0.0002 (11)	−0.0040 (13)
C8	0.0596 (18)	0.077 (2)	0.0799 (19)	−0.0239 (16)	−0.0042 (15)	0.0080 (16)
C9	0.070 (2)	0.097 (3)	0.097 (2)	−0.044 (2)	0.0083 (18)	0.004 (2)
C10	0.0465 (17)	0.112 (3)	0.095 (2)	−0.020 (2)	0.0190 (16)	−0.024 (2)
C11	0.0493 (17)	0.091 (2)	0.102 (2)	−0.0083 (17)	0.0054 (16)	−0.012 (2)
C12	0.0500 (16)	0.0664 (19)	0.0819 (19)	−0.0117 (15)	0.0070 (14)	−0.0144 (15)
C13	0.0438 (14)	0.0548 (17)	0.0609 (16)	−0.0131 (13)	0.0007 (12)	−0.0076 (13)
C14	0.0778 (19)	0.0577 (18)	0.0661 (18)	−0.0191 (15)	−0.0042 (15)	0.0006 (15)
C15	0.098 (2)	0.073 (2)	0.079 (2)	−0.009 (2)	−0.0025 (18)	0.0178 (18)
C16	0.085 (2)	0.060 (2)	0.140 (3)	−0.0107 (19)	0.010 (2)	0.028 (2)
C17	0.077 (2)	0.063 (2)	0.157 (3)	−0.0315 (19)	−0.003 (2)	0.003 (2)
C18	0.0634 (18)	0.0632 (19)	0.099 (2)	−0.0237 (16)	−0.0069 (16)	−0.0053 (18)
C19	0.0637 (18)	0.097 (2)	0.0549 (16)	−0.0298 (17)	0.0048 (14)	−0.0028 (17)
C20	0.113 (3)	0.248 (5)	0.064 (2)	−0.083 (3)	−0.0166 (19)	0.057 (3)
C21	0.111 (3)	0.144 (4)	0.114 (3)	−0.040 (3)	0.016 (2)	−0.070 (3)
C22	0.0602 (17)	0.070 (2)	0.0546 (15)	−0.0230 (15)	0.0022 (13)	0.0020 (14)
C23	0.066 (2)	0.136 (3)	0.091 (2)	−0.037 (2)	0.0027 (17)	−0.001 (2)
C24	0.124 (3)	0.062 (2)	0.097 (2)	−0.032 (2)	0.0199 (19)	0.0065 (18)
C25	0.0493 (15)	0.0511 (16)	0.0490 (15)	−0.0122 (12)	−0.0052 (12)	−0.0025 (12)
C26	0.0518 (15)	0.0522 (16)	0.0437 (14)	−0.0123 (12)	−0.0048 (11)	−0.0040 (12)
C27	0.0536 (15)	0.0720 (19)	0.0519 (15)	−0.0253 (14)	−0.0010 (12)	−0.0078 (14)
C28	0.0647 (17)	0.077 (2)	0.0461 (14)	−0.0242 (15)	−0.0061 (13)	−0.0073 (13)
C29	0.0635 (16)	0.0638 (18)	0.0488 (15)	−0.0272 (14)	0.0025 (13)	−0.0025 (13)
C30	0.083 (2)	0.106 (3)	0.0577 (17)	−0.0584 (19)	0.0008 (15)	−0.0151 (16)
C31	0.0812 (19)	0.101 (2)	0.0472 (15)	−0.0495 (18)	−0.0052 (14)	−0.0092 (15)

Geometric parameters (Å, º) top

P1—O1	1.4871 (15)	C14—H14	0.9300
P1—C13	1.789 (3)	C15—C16	1.368 (4)
P1—C7	1.794 (2)	C15—H15	0.9300
P1—C1	1.794 (2)	C16—C17	1.355 (4)
N1—O3	1.287 (2)	C16—H16	0.9300
N1—C25	1.355 (3)	C17—C18	1.382 (4)
N1—C19	1.486 (3)	C17—H17	0.9300
N2—O2	1.282 (2)	C18—H18	0.9300
N2—C25	1.349 (3)	C19—C20	1.517 (4)
N2—C22	1.491 (3)	C19—C21	1.530 (4)
O4—C29	1.356 (3)	C19—C22	1.542 (3)
O4—H4	0.8200	C20—H20A	0.9600
C1—C2	1.373 (3)	C20—H20B	0.9600
C1—C6	1.394 (3)	C20—H20C	0.9600
C2—C3	1.395 (3)	C21—H21A	0.9600
C2—H2	0.9300	C21—H21B	0.9600
C3—C4	1.366 (4)	C21—H21C	0.9600
C3—H3	0.9300	C22—C23	1.502 (3)
C4—C5	1.362 (4)	C22—C24	1.529 (4)
C4—H4A	0.9300	C23—H23A	0.9600
C5—C6	1.366 (3)	C23—H23B	0.9600
C5—H5	0.9300	C23—H23C	0.9600
C6—H6	0.9300	C24—H24A	0.9600
C7—C12	1.382 (3)	C24—H24B	0.9600
C7—C8	1.390 (4)	C24—H24C	0.9600
C8—C9	1.377 (4)	C25—C26	1.452 (3)
C8—H8	0.9300	C26—C31	1.384 (3)
C9—C10	1.370 (4)	C26—C27	1.397 (3)
C9—H9	0.9300	C27—C28	1.367 (3)
C10—C11	1.369 (4)	C27—H27	0.9300
C10—H10	0.9300	C28—C29	1.379 (3)
C11—C12	1.390 (3)	C28—H28	0.9300
C11—H11	0.9300	C29—C30	1.383 (3)
C12—H12	0.9300	C30—C31	1.367 (3)
C13—C18	1.374 (3)	C30—H30	0.9300
C13—C14	1.383 (3)	C31—H31	0.9300
C14—C15	1.381 (4)

O1—P1—C13	111.66 (11)	C16—C17—H17	120.3
O1—P1—C7	112.90 (10)	C18—C17—H17	120.3
C13—P1—C7	108.14 (12)	C13—C18—C17	121.3 (3)
O1—P1—C1	110.81 (11)	C13—C18—H18	119.4
C13—P1—C1	107.11 (11)	C17—C18—H18	119.4
C7—P1—C1	105.88 (11)	N1—C19—C20	110.5 (2)
O3—N1—C25	125.7 (2)	N1—C19—C21	105.7 (2)
O3—N1—C19	121.27 (19)	C20—C19—C21	110.5 (3)
C25—N1—C19	112.7 (2)	N1—C19—C22	100.37 (19)
O2—N2—C25	126.60 (19)	C20—C19—C22	115.7 (3)
O2—N2—C22	119.92 (19)	C21—C19—C22	113.2 (2)
C25—N2—C22	113.11 (19)	C19—C20—H20A	109.5
C29—O4—H4	109.5	C19—C20—H20B	109.5
C2—C1—C6	118.3 (2)	H20A—C20—H20B	109.5
C2—C1—P1	120.01 (19)	C19—C20—H20C	109.5
C6—C1—P1	121.70 (19)	H20A—C20—H20C	109.5
C1—C2—C3	120.5 (2)	H20B—C20—H20C	109.5
C1—C2—H2	119.8	C19—C21—H21A	109.5
C3—C2—H2	119.8	C19—C21—H21B	109.5
C4—C3—C2	119.6 (3)	H21A—C21—H21B	109.5
C4—C3—H3	120.2	C19—C21—H21C	109.5
C2—C3—H3	120.2	H21A—C21—H21C	109.5
C5—C4—C3	120.5 (3)	H21B—C21—H21C	109.5
C5—C4—H4A	119.7	N2—C22—C23	110.8 (2)
C3—C4—H4A	119.7	N2—C22—C24	106.1 (2)
C4—C5—C6	120.1 (3)	C23—C22—C24	109.8 (3)
C4—C5—H5	119.9	N2—C22—C19	99.84 (19)
C6—C5—H5	119.9	C23—C22—C19	115.4 (2)
C5—C6—C1	120.9 (3)	C24—C22—C19	114.1 (2)
C5—C6—H6	119.5	C22—C23—H23A	109.5
C1—C6—H6	119.5	C22—C23—H23B	109.5
C12—C7—C8	117.9 (2)	H23A—C23—H23B	109.5
C12—C7—P1	123.0 (2)	C22—C23—H23C	109.5
C8—C7—P1	119.0 (2)	H23A—C23—H23C	109.5
C9—C8—C7	121.3 (3)	H23B—C23—H23C	109.5
C9—C8—H8	119.4	C22—C24—H24A	109.5
C7—C8—H8	119.4	C22—C24—H24B	109.5
C10—C9—C8	119.7 (3)	H24A—C24—H24B	109.5
C10—C9—H9	120.2	C22—C24—H24C	109.5
C8—C9—H9	120.2	H24A—C24—H24C	109.5
C11—C10—C9	120.5 (3)	H24B—C24—H24C	109.5
C11—C10—H10	119.7	N2—C25—N1	106.3 (2)
C9—C10—H10	119.7	N2—C25—C26	127.0 (2)
C10—C11—C12	119.7 (3)	N1—C25—C26	126.7 (2)
C10—C11—H11	120.2	C31—C26—C27	117.1 (2)
C12—C11—H11	120.2	C31—C26—C25	121.9 (2)
C7—C12—C11	120.9 (3)	C27—C26—C25	121.0 (2)
C7—C12—H12	119.5	C28—C27—C26	121.4 (2)
C11—C12—H12	119.5	C28—C27—H27	119.3
C18—C13—C14	118.2 (3)	C26—C27—H27	119.3
C18—C13—P1	118.5 (2)	C27—C28—C29	120.7 (2)
C14—C13—P1	123.3 (2)	C27—C28—H28	119.6
C15—C14—C13	120.7 (3)	C29—C28—H28	119.6
C15—C14—H14	119.7	O4—C29—C28	123.2 (2)
C13—C14—H14	119.7	O4—C29—C30	118.4 (2)
C16—C15—C14	119.5 (3)	C28—C29—C30	118.4 (2)
C16—C15—H15	120.2	C31—C30—C29	120.8 (2)
C14—C15—H15	120.2	C31—C30—H30	119.6
C17—C16—C15	120.9 (3)	C29—C30—H30	119.6
C17—C16—H16	119.5	C30—C31—C26	121.5 (2)
C15—C16—H16	119.5	C30—C31—H31	119.3
C16—C17—C18	119.4 (3)	C26—C31—H31	119.3

O1—P1—C1—C2	15.0 (2)	C25—N1—C19—C20	146.4 (3)
C13—P1—C1—C2	−107.0 (2)	O3—N1—C19—C21	79.6 (3)
C7—P1—C1—C2	137.75 (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—C6	71.8 (2)	C25—N1—C19—C22	23.8 (3)
C7—P1—C1—C6	−43.4 (2)	O2—N2—C22—C23	−41.3 (3)
C6—C1—C2—C3	0.8 (4)	C25—N2—C22—C23	145.2 (2)
P1—C1—C2—C3	179.67 (19)	O2—N2—C22—C24	77.9 (3)
C1—C2—C3—C4	−0.7 (4)	C25—N2—C22—C24	−95.6 (2)
C2—C3—C4—C5	0.2 (4)	O2—N2—C22—C19	−163.3 (2)
C3—C4—C5—C6	0.3 (4)	C25—N2—C22—C19	23.1 (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—N2	86.6 (3)
O1—P1—C7—C12	−105.0 (2)	N1—C19—C22—C23	−144.3 (2)
C13—P1—C7—C12	19.1 (2)	C20—C19—C22—C23	96.8 (3)
C1—P1—C7—C12	133.6 (2)	C21—C19—C22—C23	−32.1 (3)
O1—P1—C7—C8	71.1 (2)	N1—C19—C22—C24	87.1 (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—N1	177.7 (2)
P1—C7—C8—C9	−176.6 (2)	C22—N2—C25—N1	−9.2 (3)
C7—C8—C9—C10	0.3 (5)	O2—N2—C25—C26	−1.2 (4)
C8—C9—C10—C11	−0.5 (5)	C22—N2—C25—C26	171.8 (2)
C9—C10—C11—C12	0.8 (5)	O3—N1—C25—N2	176.5 (2)
C8—C7—C12—C11	0.6 (4)	C19—N1—C25—N2	−10.1 (3)
P1—C7—C12—C11	176.8 (2)	O3—N1—C25—C26	−4.5 (4)
C10—C11—C12—C7	−0.9 (4)	C19—N1—C25—C26	168.8 (2)
O1—P1—C13—C18	−0.2 (2)	N2—C25—C26—C31	161.1 (2)
C7—P1—C13—C18	−125.0 (2)	N1—C25—C26—C31	−17.7 (4)
C1—P1—C13—C18	121.3 (2)	N2—C25—C26—C27	−18.9 (4)
O1—P1—C13—C14	−178.3 (2)	N1—C25—C26—C27	162.4 (2)
C7—P1—C13—C14	56.9 (2)	C31—C26—C27—C28	−1.0 (4)
C1—P1—C13—C14	−56.8 (2)	C25—C26—C27—C28	178.9 (2)
C18—C13—C14—C15	−0.5 (4)	C26—C27—C28—C29	0.2 (4)
P1—C13—C14—C15	177.6 (2)	C27—C28—C29—O4	−179.8 (2)
C13—C14—C15—C16	−0.5 (4)	C27—C28—C29—C30	0.0 (4)
C14—C15—C16—C17	1.2 (5)	O4—C29—C30—C31	−179.5 (3)
C15—C16—C17—C18	−0.7 (5)	C28—C29—C30—C31	0.6 (4)
C14—C13—C18—C17	1.0 (4)	C29—C30—C31—C26	−1.5 (5)
P1—C13—C18—C17	−177.2 (2)	C27—C26—C31—C30	1.6 (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, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1ⁱ	0.82	1.82	2.633 (2)	171

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅OP·C₁₃H₁₇N₂O₃
M_r	527.56
Crystal system, space group	Triclinic, 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)
V (Å³)	1442.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.39 × 0.28 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.951, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	7342, 5071, 2859
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.124, 1.08
No. of reflections	5071
No. of parameters	349
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
O4—H4···O1ⁱ	0.820	1.821	2.633 (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

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

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Volume 65| Part 10| October 2009| Page o2444

doi:10.1107/S160053680903356X

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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