Triphenyl-phosphine oxide-2-(4-hydroxy-benzen-yl)-4,4,5,5-tetra-methyl-imidazolidine-1-oxyl 3-oxide (1/1).

The title compound, C(18)H(15)OP·C(13)H(17)N(2)O(3), belongs to a series of mol-ecular systems based on triphenyl-phosphine 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 = 527.56

Triclinic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 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

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H15OP·C13H17N2O3	Z = 2
Mr = 527.56	F(000) = 558
Triclinic, P1	Dx = 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

Bruker APEXII CCD area-detector diffractometer	5071 independent reflections
Radiation source: fine-focus sealed tube	2859 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
Tmin = 0.951, Tmax = 0.979	k = −9→14
7342 measured reflections	l = −16→16

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(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
5071 reflections	Δρmax = 0.20 e Å−3
349 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .