Di-aqua-{μ2-N,N'-bis-[(cyclo-hexa-nyl-idene)amino]-oxamide}-bis-(tri-phenyl-phosphane)silver(I) dinitrate.

The dinuclear title compound, [Ag2(C14H22N4O2)(C18H15P)2(H2O)2](NO3)2, lies across an inversion center and consists of two [Ag(H2O)(PPh3)] units bridged by a bis-(cyclo-hexa-none)oxalydihydrazone ligand. The charge-balance is supplied by two nitrate anions. The symmetry-unique Ag(I) ion is in a distorted tetra-hedral geometry coordinated by a P atom from a tri-phenyl-phosphane ligand, an O atom from a water mol-ecule and a bis-(cyclo-hexa-none)oxalydihydrazone ligand bidentate chelating through the O atom and one of N atoms. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link the components, forming chains along the b-axis direction. These chains are connected through weak C-H⋯O hydrogen bonds, leading to the formation of a two-dimensional supra-molecular network parallel to (001).

Related literature

For potential applications of hydrazone derivatives, see: Fouda et al. (2007 ▶); Qu et al. (2011 ▶); van der Star et al. (2012 ▶). For the use of metal(I) complexes of phosphine ligands as precursors for the preparation of mixed-ligand complexes, see: Nawaz et al. (2011 ▶); Pakawatchai et al. (2012 ▶). For a related structure, see: Wattanakanjana et al. (2013 ▶).

Experimental

Crystal data

n class="Chemical">[Ag2(C14H22N4O2)(C18H15P)2(H2O)2](NO3)2

M = 1178.68

Trin class="Chemical">clinin class="Chemical">c,

a = 9.0903 (8) Å

b = 9.5730 (8) Å

n class="Chemical">c = 15.2638 (13) Å

α = 74.617 (1)°

β = 83.676 (1)°

γ = 77.091 (1)°

V = 1246.49 (18) Å3

Z = 1

Mo Kα radiation

μ = 0.91 mm−1

T = 100 K

0.42 × 0.38 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T min = 0.624, T max = 0.746

29613 measured reflen class="Chemical">ctions

7621 independent reflen class="Chemical">ctions

7076 reflen class="Chemical">ctions with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.072

S = 1.02

7621 reflen class="Chemical">ctions

313 parameters

H-atom parameters n class="Chemical">constrained

Δρmax = 1.50 e Å−3

Δρmin = −0.54 e Å−3

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶), SHELXLE (Hübschle et al., 2011 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813034454/lh5679sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034454/lh5679Isup2.hkl

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Ag2(C14H22N4O2)(C18H15P)2(H2O)2](NO3)2	Z = 1
Mr = 1178.68	F(000) = 602
Triclinic, P1	Dx = 1.570 Mg m−3
a = 9.0903 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5730 (8) Å	Cell parameters from 6878 reflections
c = 15.2638 (13) Å	θ = 2.3–31.3°
α = 74.617 (1)°	µ = 0.91 mm−1
β = 83.676 (1)°	T = 100 K
γ = 77.091 (1)°	Plate, colourless
V = 1246.49 (18) Å3	0.42 × 0.38 × 0.10 mm

Bruker SMART APEX CCD diffractometer	7076 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.032
φ and ω scans	θmax = 31.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −13→13
Tmin = 0.624, Tmax = 0.746	k = −13→13
29613 measured reflections	l = −22→22
7621 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028	Hydrogen site location: mixed
wR(F2) = 0.072	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0427P)2 + 0.444P] where P = (Fo2 + 2Fc2)/3
7621 reflections	(Δ/σ)max = 0.001
313 parameters	Δρmax = 1.50 e Å−3
0 restraints	Δρmin = −0.54 e Å−3

Experimental. Reflections 0 0 1 was affected by the beam stop and was omitted from the refinement.

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.

	x	y	z	Uiso*/Ueq
Ag1	0.77397 (2)	0.67531 (2)	0.14033 (2)	0.01512 (4)
P1	0.87389 (4)	0.59821 (4)	0.28403 (3)	0.01204 (7)
O1	0.58233 (10)	0.91020 (10)	0.10413 (6)	0.0182 (2)
O2	0.60176 (10)	0.57786 (10)	0.07530 (6)	0.0278 (3)
H2A	0.5453	0.5216	0.0951	0.042*
H2B	0.5935	0.5990	0.0158	0.042*
O3	0.41980 (18)	0.36454 (16)	0.11758 (9)	0.0311 (3)
O4	0.46973 (17)	0.30464 (18)	0.26020 (10)	0.0327 (3)
O5	0.37588 (17)	0.15741 (16)	0.20689 (9)	0.0289 (3)
N1	0.67258 (14)	0.90320 (14)	−0.04115 (9)	0.0146 (2)
H1	0.6597	0.9387	−0.0998	0.017*
N2	0.80176 (14)	0.79893 (14)	−0.00875 (9)	0.0144 (2)
N3	0.42173 (16)	0.27494 (17)	0.19571 (10)	0.0211 (3)
C1	0.56953 (16)	0.94638 (16)	0.02131 (10)	0.0132 (3)
C2	0.91980 (17)	0.79182 (17)	−0.06359 (10)	0.0160 (3)
C3	0.93888 (19)	0.88935 (19)	−0.15685 (11)	0.0203 (3)
H3A	0.8466	0.9672	−0.1707	0.024*
H3B	0.9540	0.8301	−0.2025	0.024*
C4	1.0763 (2)	0.96139 (19)	−0.16206 (12)	0.0220 (3)
H4A	1.0959	1.0152	−0.2258	0.026*
H4B	1.0528	1.0343	−0.1245	0.026*
C5	1.21787 (19)	0.8478 (2)	−0.12903 (12)	0.0222 (3)
H5A	1.2474	0.7802	−0.1699	0.027*
H5B	1.3020	0.8989	−0.1309	0.027*
C6	1.19021 (19)	0.75881 (19)	−0.03247 (12)	0.0210 (3)
H6A	1.1659	0.8255	0.0091	0.025*
H6B	1.2827	0.6846	−0.0123	0.025*
C7	1.05827 (18)	0.68022 (18)	−0.02872 (11)	0.0185 (3)
H7A	1.0861	0.6074	−0.0663	0.022*
H7B	1.0371	0.6264	0.0348	0.022*
C11	0.74414 (17)	0.67524 (18)	0.36679 (11)	0.0163 (3)
C12	0.66381 (18)	0.82024 (19)	0.33780 (12)	0.0204 (3)
H12	0.6780	0.8747	0.2768	0.024*
C13	0.5628 (2)	0.8854 (2)	0.39823 (15)	0.0289 (4)
H13	0.5084	0.9842	0.3786	0.035*
C14	0.5425 (2)	0.8049 (3)	0.48700 (15)	0.0347 (5)
H14	0.4741	0.8492	0.5284	0.042*
C15	0.6211 (2)	0.6599 (3)	0.51627 (14)	0.0338 (4)
H15	0.6058	0.6054	0.5772	0.041*
C16	0.7224 (2)	0.5946 (2)	0.45616 (12)	0.0244 (3)
H16	0.7765	0.4957	0.4759	0.029*
C21	0.91018 (18)	0.39933 (16)	0.33027 (10)	0.0146 (3)
C22	0.7932 (2)	0.32645 (19)	0.32916 (11)	0.0201 (3)
H22	0.6984	0.3814	0.3067	0.024*
C23	0.8160 (2)	0.1736 (2)	0.36097 (12)	0.0262 (4)
H23	0.7362	0.1240	0.3613	0.031*
C24	0.9551 (3)	0.0933 (2)	0.39231 (13)	0.0297 (4)
H24	0.9703	−0.0113	0.4139	0.036*
C25	1.0718 (3)	0.1643 (2)	0.39229 (14)	0.0309 (4)
H25	1.1671	0.1084	0.4132	0.037*
C26	1.0499 (2)	0.31784 (19)	0.36159 (12)	0.0222 (3)
H26	1.1299	0.3667	0.3620	0.027*
C31	1.05027 (17)	0.65300 (16)	0.29052 (11)	0.0152 (3)
C32	1.07908 (19)	0.70550 (18)	0.36258 (12)	0.0204 (3)
H32	1.0065	0.7101	0.4120	0.025*
C33	1.2145 (2)	0.7513 (2)	0.36192 (15)	0.0296 (4)
H33	1.2338	0.7877	0.4108	0.036*
C34	1.3209 (2)	0.7438 (2)	0.29016 (16)	0.0337 (4)
H34	1.4121	0.7769	0.2895	0.040*
C35	1.2953 (2)	0.6887 (3)	0.21933 (15)	0.0322 (4)
H35	1.3696	0.6816	0.1709	0.039*
C36	1.1601 (2)	0.6437 (2)	0.21948 (13)	0.0243 (3)
H36	1.1421	0.6062	0.1708	0.029*

	U11	U22	U33	U12	U13	U23
Ag1	0.01432 (6)	0.01811 (6)	0.01070 (6)	0.00005 (4)	−0.00308 (4)	−0.00155 (4)
P1	0.01111 (16)	0.01418 (16)	0.01055 (16)	−0.00195 (13)	−0.00170 (12)	−0.00267 (13)
O1	0.0195 (5)	0.0194 (5)	0.0129 (5)	0.0032 (4)	−0.0034 (4)	−0.0040 (4)
O2	0.0328 (7)	0.0370 (7)	0.0208 (6)	−0.0188 (6)	−0.0022 (5)	−0.0096 (5)
O3	0.0411 (8)	0.0359 (7)	0.0194 (6)	−0.0171 (6)	−0.0039 (6)	−0.0038 (5)
O4	0.0329 (7)	0.0479 (9)	0.0250 (7)	−0.0109 (6)	−0.0062 (6)	−0.0180 (6)
O5	0.0355 (7)	0.0358 (7)	0.0203 (6)	−0.0179 (6)	0.0022 (5)	−0.0078 (5)
N1	0.0128 (6)	0.0159 (6)	0.0118 (5)	0.0001 (5)	−0.0018 (4)	0.0000 (5)
N2	0.0106 (5)	0.0161 (6)	0.0137 (6)	0.0000 (4)	−0.0011 (4)	−0.0010 (5)
N3	0.0161 (6)	0.0308 (7)	0.0187 (6)	−0.0047 (6)	0.0005 (5)	−0.0107 (6)
C1	0.0121 (6)	0.0127 (6)	0.0146 (6)	−0.0020 (5)	−0.0030 (5)	−0.0023 (5)
C2	0.0140 (7)	0.0186 (7)	0.0151 (7)	−0.0040 (5)	−0.0003 (5)	−0.0034 (5)
C3	0.0171 (7)	0.0265 (8)	0.0140 (7)	−0.0055 (6)	0.0016 (5)	0.0005 (6)
C4	0.0216 (8)	0.0230 (8)	0.0205 (8)	−0.0075 (6)	0.0036 (6)	−0.0033 (6)
C5	0.0177 (7)	0.0277 (8)	0.0237 (8)	−0.0084 (6)	0.0026 (6)	−0.0092 (7)
C6	0.0151 (7)	0.0267 (8)	0.0219 (8)	−0.0028 (6)	−0.0003 (6)	−0.0088 (6)
C7	0.0139 (7)	0.0193 (7)	0.0203 (7)	−0.0008 (6)	−0.0003 (6)	−0.0041 (6)
C11	0.0124 (6)	0.0231 (7)	0.0168 (7)	−0.0053 (6)	0.0005 (5)	−0.0095 (6)
C12	0.0148 (7)	0.0222 (7)	0.0286 (8)	−0.0055 (6)	0.0001 (6)	−0.0131 (7)
C13	0.0178 (8)	0.0323 (9)	0.0458 (11)	−0.0070 (7)	0.0044 (7)	−0.0266 (9)
C14	0.0253 (9)	0.0514 (12)	0.0426 (11)	−0.0163 (9)	0.0126 (8)	−0.0367 (10)
C15	0.0325 (10)	0.0552 (13)	0.0228 (9)	−0.0190 (9)	0.0096 (7)	−0.0213 (9)
C16	0.0246 (8)	0.0339 (9)	0.0160 (7)	−0.0081 (7)	0.0016 (6)	−0.0079 (7)
C21	0.0181 (7)	0.0148 (6)	0.0109 (6)	−0.0044 (5)	−0.0003 (5)	−0.0022 (5)
C22	0.0209 (8)	0.0215 (7)	0.0201 (7)	−0.0086 (6)	0.0028 (6)	−0.0069 (6)
C23	0.0357 (10)	0.0241 (8)	0.0231 (8)	−0.0164 (7)	0.0103 (7)	−0.0094 (7)
C24	0.0493 (12)	0.0160 (7)	0.0212 (8)	−0.0078 (8)	0.0020 (8)	−0.0008 (6)
C25	0.0383 (11)	0.0196 (8)	0.0289 (9)	0.0019 (7)	−0.0101 (8)	0.0010 (7)
C26	0.0249 (8)	0.0183 (7)	0.0213 (8)	−0.0020 (6)	−0.0074 (6)	−0.0005 (6)
C31	0.0128 (6)	0.0141 (6)	0.0180 (7)	−0.0027 (5)	−0.0029 (5)	−0.0021 (5)
C32	0.0175 (7)	0.0209 (7)	0.0248 (8)	−0.0042 (6)	−0.0044 (6)	−0.0073 (6)
C33	0.0219 (8)	0.0336 (10)	0.0408 (11)	−0.0080 (7)	−0.0083 (8)	−0.0173 (8)
C34	0.0171 (8)	0.0388 (11)	0.0508 (13)	−0.0101 (8)	−0.0037 (8)	−0.0163 (9)
C35	0.0167 (8)	0.0450 (11)	0.0377 (11)	−0.0099 (8)	0.0055 (7)	−0.0147 (9)
C36	0.0175 (8)	0.0337 (9)	0.0253 (8)	−0.0082 (7)	0.0026 (6)	−0.0123 (7)

Ag1—N2	2.2849 (13)	C11—C16	1.395 (2)
Ag1—P1	2.3369 (4)	C11—C12	1.396 (2)
Ag1—O2	2.4068	C12—C13	1.395 (2)
Ag1—O1	2.4898 (9)	C12—H12	0.9500
P1—C21	1.8137 (15)	C13—C14	1.385 (3)
P1—C31	1.8149 (16)	C13—H13	0.9500
P1—C11	1.8187 (16)	C14—C15	1.391 (3)
O1—C1	1.2304 (17)	C14—H14	0.9500
O2—H2A	0.8048	C15—C16	1.393 (3)
O2—H2B	0.8848	C15—H15	0.9500
O3—N3	1.270 (2)	C16—H16	0.9500
O4—N3	1.2404 (19)	C21—C26	1.394 (2)
O5—N3	1.249 (2)	C21—C22	1.400 (2)
N1—C1	1.340 (2)	C22—C23	1.389 (2)
N1—N2	1.4008 (17)	C22—H22	0.9500
N1—H1	0.8800	C23—C24	1.387 (3)
N2—C2	1.287 (2)	C23—H23	0.9500
C1—C1i	1.524 (3)	C24—C25	1.382 (3)
C2—C3	1.497 (2)	C24—H24	0.9500
C2—C7	1.501 (2)	C25—C26	1.394 (2)
C3—C4	1.542 (2)	C25—H25	0.9500
C3—H3A	0.9900	C26—H26	0.9500
C3—H3B	0.9900	C31—C32	1.395 (2)
C4—C5	1.523 (2)	C31—C36	1.398 (2)
C4—H4A	0.9900	C32—C33	1.394 (2)
C4—H4B	0.9900	C32—H32	0.9500
C5—C6	1.519 (2)	C33—C34	1.385 (3)
C5—H5A	0.9900	C33—H33	0.9500
C5—H5B	0.9900	C34—C35	1.384 (3)
C6—C7	1.541 (2)	C34—H34	0.9500
C6—H6A	0.9900	C35—C36	1.390 (3)
C6—H6B	0.9900	C35—H35	0.9500
C7—H7A	0.9900	C36—H36	0.9500
C7—H7B	0.9900
N2—Ag1—P1	146.83 (3)	C2—C7—H7B	109.7
N2—Ag1—O2	80.48 (4)	C6—C7—H7B	109.7
P1—Ag1—O2	130.70 (2)	H7A—C7—H7B	108.2
N2—Ag1—O1	69.04 (4)	C16—C11—C12	120.00 (15)
P1—Ag1—O1	118.43 (2)	C16—C11—P1	122.44 (13)
O2—Ag1—O1	84.40 (3)	C12—C11—P1	117.56 (12)
C21—P1—C31	105.26 (7)	C13—C12—C11	120.17 (17)
C21—P1—C11	105.67 (7)	C13—C12—H12	119.9
C31—P1—C11	104.89 (7)	C11—C12—H12	119.9
C21—P1—Ag1	113.89 (5)	C14—C13—C12	119.49 (19)
C31—P1—Ag1	115.29 (5)	C14—C13—H13	120.3
C11—P1—Ag1	110.99 (5)	C12—C13—H13	120.3
C1—O1—Ag1	107.71 (8)	C13—C14—C15	120.72 (17)
Ag1—O2—H2A	135.1	C13—C14—H14	119.6
Ag1—O2—H2B	121.5	C15—C14—H14	119.6
H2A—O2—H2B	103.3	C14—C15—C16	119.94 (19)
C1—N1—N2	116.91 (12)	C14—C15—H15	120.0
C1—N1—H1	121.5	C16—C15—H15	120.0
N2—N1—H1	121.5	C15—C16—C11	119.67 (19)
C2—N2—N1	117.05 (13)	C15—C16—H16	120.2
C2—N2—Ag1	129.26 (11)	C11—C16—H16	120.2
N1—N2—Ag1	113.55 (9)	C26—C21—C22	119.82 (15)
O4—N3—O5	120.55 (16)	C26—C21—P1	122.88 (12)
O4—N3—O3	119.69 (16)	C22—C21—P1	117.21 (12)
O5—N3—O3	119.76 (14)	C23—C22—C21	119.81 (17)
O1—C1—N1	125.99 (13)	C23—C22—H22	120.1
O1—C1—C1i	121.54 (17)	C21—C22—H22	120.1
N1—C1—C1i	112.43 (16)	C24—C23—C22	120.06 (17)
N2—C2—C3	127.37 (15)	C24—C23—H23	120.0
N2—C2—C7	117.00 (14)	C22—C23—H23	120.0
C3—C2—C7	115.50 (13)	C25—C24—C23	120.41 (16)
C2—C3—C4	109.85 (14)	C25—C24—H24	119.8
C2—C3—H3A	109.7	C23—C24—H24	119.8
C4—C3—H3A	109.7	C24—C25—C26	120.14 (18)
C2—C3—H3B	109.7	C24—C25—H25	119.9
C4—C3—H3B	109.7	C26—C25—H25	119.9
H3A—C3—H3B	108.2	C21—C26—C25	119.75 (17)
C5—C4—C3	112.15 (14)	C21—C26—H26	120.1
C5—C4—H4A	109.2	C25—C26—H26	120.1
C3—C4—H4A	109.2	C32—C31—C36	119.17 (15)
C5—C4—H4B	109.2	C32—C31—P1	122.66 (12)
C3—C4—H4B	109.2	C36—C31—P1	118.16 (12)
H4A—C4—H4B	107.9	C33—C32—C31	119.95 (17)
C6—C5—C4	110.70 (14)	C33—C32—H32	120.0
C6—C5—H5A	109.5	C31—C32—H32	120.0
C4—C5—H5A	109.5	C34—C33—C32	120.11 (18)
C6—C5—H5B	109.5	C34—C33—H33	119.9
C4—C5—H5B	109.5	C32—C33—H33	119.9
H5A—C5—H5B	108.1	C35—C34—C33	120.54 (17)
C5—C6—C7	109.82 (14)	C35—C34—H34	119.7
C5—C6—H6A	109.7	C33—C34—H34	119.7
C7—C6—H6A	109.7	C34—C35—C36	119.52 (18)
C5—C6—H6B	109.7	C34—C35—H35	120.2
C7—C6—H6B	109.7	C36—C35—H35	120.2
H6A—C6—H6B	108.2	C35—C36—C31	120.69 (17)
C2—C7—C6	109.86 (13)	C35—C36—H36	119.7
C2—C7—H7A	109.7	C31—C36—H36	119.7
C6—C7—H7A	109.7
C1—N1—N2—C2	−158.29 (14)	C12—C11—C16—C15	−0.4 (3)
C1—N1—N2—Ag1	17.79 (16)	P1—C11—C16—C15	−179.89 (14)
Ag1—O1—C1—N1	−22.20 (17)	C31—P1—C21—C26	−0.36 (16)
Ag1—O1—C1—C1i	160.03 (15)	C11—P1—C21—C26	−111.04 (14)
N2—N1—C1—O1	5.0 (2)	Ag1—P1—C21—C26	126.88 (13)
N2—N1—C1—C1i	−177.05 (14)	C31—P1—C21—C22	−176.91 (12)
N1—N2—C2—C3	4.3 (2)	C11—P1—C21—C22	72.41 (13)
Ag1—N2—C2—C3	−171.05 (12)	Ag1—P1—C21—C22	−49.67 (13)
N1—N2—C2—C7	179.89 (13)	C26—C21—C22—C23	1.3 (2)
Ag1—N2—C2—C7	4.5 (2)	P1—C21—C22—C23	177.95 (13)
N2—C2—C3—C4	123.63 (18)	C21—C22—C23—C24	−1.1 (3)
C7—C2—C3—C4	−52.01 (19)	C22—C23—C24—C25	0.1 (3)
C2—C3—C4—C5	51.65 (19)	C23—C24—C25—C26	0.7 (3)
C3—C4—C5—C6	−56.69 (19)	C22—C21—C26—C25	−0.5 (3)
C4—C5—C6—C7	58.54 (18)	P1—C21—C26—C25	−176.97 (14)
N2—C2—C7—C6	−121.04 (16)	C24—C25—C26—C21	−0.5 (3)
C3—C2—C7—C6	55.07 (19)	C21—P1—C31—C32	−95.87 (14)
C5—C6—C7—C2	−56.55 (18)	C11—P1—C31—C32	15.37 (15)
C21—P1—C11—C16	17.38 (16)	Ag1—P1—C31—C32	137.74 (12)
C31—P1—C11—C16	−93.57 (15)	C21—P1—C31—C36	85.04 (14)
Ag1—P1—C11—C16	141.31 (13)	C11—P1—C31—C36	−163.72 (13)
C21—P1—C11—C12	−162.09 (12)	Ag1—P1—C31—C36	−41.35 (15)
C31—P1—C11—C12	86.96 (13)	C36—C31—C32—C33	1.6 (3)
Ag1—P1—C11—C12	−38.16 (13)	P1—C31—C32—C33	−177.50 (14)
C16—C11—C12—C13	0.6 (2)	C31—C32—C33—C34	−0.4 (3)
P1—C11—C12—C13	−179.91 (13)	C32—C33—C34—C35	−1.1 (3)
C11—C12—C13—C14	−0.2 (3)	C33—C34—C35—C36	1.5 (3)
C12—C13—C14—C15	−0.3 (3)	C34—C35—C36—C31	−0.3 (3)
C13—C14—C15—C16	0.5 (3)	C32—C31—C36—C35	−1.2 (3)
C14—C15—C16—C11	−0.1 (3)	P1—C31—C36—C35	177.89 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3	0.80	2.02	2.8103 (17)	167
O2—H2B···O3ii	0.88	1.98	2.8684 (16)	177
N1—H1···O5ii	0.88	2.16	2.8407 (19)	134
C22—H22···O4	0.95	2.58	3.297 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3	0.80	2.02	2.8103 (17)	167
O2—H2B⋯O3i	0.88	1.98	2.8684 (16)	177
N1—H1⋯O5i	0.88	2.16	2.8407 (19)	134
C22—H22⋯O4	0.95	2.58	3.297 (2)	133

Symmetry code: (i) .