catena-Poly[[silver(I)-μ-4,4'-bipyridine-κ(2)N:N'] 4-[2-(4-carb-oxy-phen-yl)-1,1,1,3,3,3-hexa-fluoro-propan-2-yl]benzoate].

Assembly of the flexible dicarb-oxy-lic ligand 4-[2-(4-carboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzoate and 4,4'-bipyridine as co-ligand with Ag(I) ions resulted in the formation of the polymeric title compound, {[Ag(C(10)H(8)N(2))](C(17)H(9)F(6)O(4))}(n), in which the metal atoms are bridged by the 4,4'-bipyridine ligands, generating cationic chains extending along [010]. The dihedral angles between the benzene rings in the anion and the pyridine rings in the cation are 72.42 (9) and 9.36 (10)°, respectively. The mol-ecular conformation of the anion is stabilized by intra-molecular C-H⋯F hydrogen bonds. In the crystal, the anions inter-act with the cationic chains via C-H⋯O hydrogen bonds, forming layers parallel to (001), in which weak π-π stacking inter-actions [centroid-centroid distances = 3.975 (3)-4.047 (3) Å] involving the pyridine rings of adjacent 4,4'-bipyridine ligands are present. The planes are further assembled into a three-dimensional network by O-H⋯O hydrogen bonds.

Related literature

For background to metal-organic frameworks, see: Du et al. (2007 ▶); Li & Du (2011 ▶); Hosseini (2005 ▶). For metallosupra­molecular architectures, see: Brammer (2004 ▶); Peedikakkal & Vittal (2011 ▶). For coordination frameworks constructed from pyridyl and carboxyl­ate spacers, see: Li et al. (2012 ▶). For weak cooperative inter­molecular inter­actions, see: Ye et al. (2005 ▶). For flexible polycarboxyl ligands, see: Liu et al. (2011 ▶). For the structures of metal complexes derived from 4-[2-(4-carboxy­phenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzoate, see: Jiang et al. (2009 ▶); Ji et al. (2010 ▶).

Experimental

Crystal data

[Ag(C10H8N2)](C17H9F6O4)

M = 655.30

Monoclinic,

a = 16.434 (7) Å

b = 11.436 (5) Å

c = 14.320 (6) Å

β = 104.310 (7)°

V = 2607.9 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.85 mm−1

T = 296 K

0.24 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.817, T max = 0.862

12604 measured reflections

4604 independent reflections

3593 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.080

S = 1.06

4604 reflections

362 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015322/rz2731sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015322/rz2731Isup2.hkl

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

[Ag(C10H8N2)](C17H9F6O4)	F(000) = 1304
Mr = 655.30	Dx = 1.669 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3592 reflections
a = 16.434 (7) Å	θ = 2.6–25.0°
b = 11.436 (5) Å	µ = 0.85 mm−1
c = 14.320 (6) Å	T = 296 K
β = 104.310 (7)°	Block, colourless
V = 2607.9 (19) Å3	0.24 × 0.20 × 0.18 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4604 independent reflections
Radiation source: fine-focus sealed tube	3593 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
phi and ω scans	θmax = 25.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −19→18
Tmin = 0.817, Tmax = 0.862	k = −13→11
12604 measured reflections	l = −13→17

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0345P)2 + 0.8598P] where P = (Fo2 + 2Fc2)/3
4604 reflections	(Δ/σ)max = 0.001
362 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

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
Ag1	0.530651 (16)	−0.082641 (18)	0.622126 (19)	0.04658 (10)
F1	0.02974 (15)	0.6454 (2)	0.92201 (18)	0.0909 (8)
F2	0.06031 (13)	0.61728 (17)	0.78671 (18)	0.0684 (6)
F3	0.15860 (14)	0.6401 (2)	0.91554 (16)	0.0829 (7)
F4	0.09383 (15)	0.8354 (2)	1.01974 (14)	0.0868 (8)
F5	0.10424 (14)	0.9881 (2)	0.93702 (15)	0.0757 (7)
F6	0.20357 (13)	0.8623 (3)	0.96704 (15)	0.0886 (8)
O1	−0.32135 (14)	0.9301 (2)	0.75562 (17)	0.0601 (7)
O2	−0.31043 (12)	0.90448 (18)	0.60650 (15)	0.0447 (5)
O3	0.33356 (15)	0.9023 (2)	0.56863 (18)	0.0608 (7)
O4	0.24921 (14)	1.05711 (19)	0.53684 (16)	0.0484 (6)
H4	0.2713	1.0657	0.4919	0.073*
N1	0.52282 (16)	0.7266 (2)	0.62575 (17)	0.0404 (6)
N2	0.51817 (15)	0.1071 (2)	0.61686 (17)	0.0368 (6)
C1	0.58883 (19)	0.2880 (2)	0.6165 (2)	0.0423 (8)
H1	0.6375	0.3270	0.6123	0.051*
C2	0.5861 (2)	0.1688 (2)	0.6116 (2)	0.0424 (8)
H2	0.6334	0.1288	0.6043	0.051*
C3	0.4518 (2)	0.1674 (3)	0.6274 (2)	0.0449 (8)
H3	0.4039	0.1262	0.6306	0.054*
C4	0.45017 (19)	0.2870 (2)	0.6337 (2)	0.0412 (8)
H4A	0.4023	0.3247	0.6421	0.049*
C5	0.52023 (17)	0.3515 (2)	0.62763 (19)	0.0314 (7)
C6	0.52118 (18)	0.4813 (2)	0.63058 (19)	0.0331 (7)
C7	0.44988 (19)	0.5469 (2)	0.6263 (2)	0.0398 (7)
H7	0.3993	0.5096	0.6251	0.048*
C8	0.4531 (2)	0.6668 (2)	0.6239 (2)	0.0416 (8)
H8	0.4038	0.7083	0.6207	0.050*
C9	0.5923 (2)	0.6642 (3)	0.6312 (3)	0.0568 (10)
H9	0.6421	0.7040	0.6331	0.068*
C10	0.5941 (2)	0.5440 (3)	0.6341 (3)	0.0545 (9)
H10	0.6445	0.5046	0.6385	0.065*
C11	−0.27936 (19)	0.9090 (2)	0.6968 (2)	0.0399 (7)
C12	−0.18662 (18)	0.8837 (3)	0.7344 (2)	0.0385 (7)
C13	−0.13701 (19)	0.8418 (3)	0.6766 (2)	0.0410 (7)
H13	−0.1609	0.8275	0.6117	0.049*
C14	−0.05230 (19)	0.8210 (3)	0.7143 (2)	0.0430 (8)
H14	−0.0199	0.7935	0.6741	0.052*
C15	−0.01503 (19)	0.8405 (3)	0.8103 (2)	0.0396 (7)
C16	−0.0646 (2)	0.8806 (3)	0.8685 (2)	0.0558 (9)
H16	−0.0410	0.8934	0.9337	0.067*
C17	−0.1491 (2)	0.9019 (3)	0.8306 (2)	0.0538 (9)
H17	−0.1814	0.9291	0.8710	0.065*
C18	0.07922 (19)	0.8103 (3)	0.8496 (2)	0.0434 (8)
C19	0.0819 (2)	0.6771 (4)	0.8687 (3)	0.0611 (10)
C20	0.1197 (2)	0.8734 (4)	0.9440 (3)	0.0638 (10)
C21	0.13085 (18)	0.8446 (3)	0.7768 (2)	0.0389 (7)
C22	0.1201 (2)	0.9558 (3)	0.7381 (2)	0.0479 (8)
H22	0.0809	1.0055	0.7542	0.057*
C23	0.1665 (2)	0.9947 (3)	0.6759 (2)	0.0472 (8)
H23	0.1586	1.0702	0.6512	0.057*
C24	0.22482 (18)	0.9221 (3)	0.6502 (2)	0.0387 (7)
C25	0.2352 (2)	0.8112 (3)	0.6884 (2)	0.0461 (8)
H25	0.2740	0.7615	0.6716	0.055*
C26	0.18943 (19)	0.7715 (3)	0.7511 (2)	0.0452 (8)
H26	0.1978	0.6962	0.7761	0.054*
C27	0.27476 (19)	0.9585 (3)	0.5814 (2)	0.0408 (7)

	U11	U22	U33	U12	U13	U23
Ag1	0.04784 (17)	0.02023 (13)	0.06987 (19)	0.00120 (10)	0.01111 (12)	−0.00107 (11)
F1	0.0822 (18)	0.0897 (17)	0.116 (2)	0.0119 (14)	0.0525 (16)	0.0463 (15)
F2	0.0601 (14)	0.0440 (11)	0.1002 (17)	0.0030 (10)	0.0179 (12)	0.0053 (12)
F3	0.0614 (15)	0.0972 (17)	0.0862 (16)	0.0294 (13)	0.0110 (12)	0.0452 (14)
F4	0.0702 (16)	0.150 (2)	0.0394 (12)	0.0082 (15)	0.0126 (11)	0.0089 (13)
F5	0.0730 (16)	0.0876 (17)	0.0653 (14)	−0.0097 (13)	0.0145 (11)	−0.0295 (13)
F6	0.0400 (13)	0.155 (2)	0.0620 (13)	0.0041 (14)	−0.0043 (10)	−0.0173 (15)
O1	0.0368 (14)	0.0868 (19)	0.0628 (15)	0.0103 (12)	0.0241 (12)	−0.0029 (13)
O2	0.0298 (12)	0.0521 (14)	0.0524 (14)	−0.0024 (10)	0.0106 (10)	0.0057 (11)
O3	0.0441 (15)	0.0664 (17)	0.0788 (17)	0.0175 (12)	0.0285 (13)	0.0164 (13)
O4	0.0456 (14)	0.0492 (13)	0.0532 (14)	0.0041 (11)	0.0173 (11)	0.0054 (11)
N1	0.0398 (16)	0.0243 (13)	0.0561 (16)	0.0021 (11)	0.0095 (12)	−0.0007 (11)
N2	0.0363 (16)	0.0247 (13)	0.0467 (15)	0.0017 (10)	0.0050 (12)	−0.0012 (10)
C1	0.0346 (18)	0.0278 (15)	0.066 (2)	−0.0027 (13)	0.0154 (16)	0.0025 (14)
C2	0.0369 (19)	0.0289 (15)	0.064 (2)	0.0056 (13)	0.0182 (16)	0.0020 (15)
C3	0.038 (2)	0.0294 (16)	0.066 (2)	−0.0050 (14)	0.0113 (16)	0.0012 (15)
C4	0.0319 (18)	0.0280 (15)	0.065 (2)	0.0019 (12)	0.0147 (15)	0.0002 (14)
C5	0.0338 (18)	0.0251 (15)	0.0343 (15)	0.0030 (12)	0.0064 (13)	0.0000 (12)
C6	0.0368 (18)	0.0236 (15)	0.0393 (17)	−0.0010 (12)	0.0102 (13)	−0.0002 (12)
C7	0.0333 (18)	0.0265 (15)	0.063 (2)	0.0005 (12)	0.0177 (15)	0.0014 (14)
C8	0.038 (2)	0.0272 (15)	0.063 (2)	0.0080 (13)	0.0193 (16)	0.0023 (14)
C9	0.038 (2)	0.0297 (17)	0.101 (3)	−0.0049 (14)	0.0131 (19)	−0.0053 (18)
C10	0.0336 (19)	0.0281 (16)	0.100 (3)	0.0026 (14)	0.0124 (18)	−0.0043 (17)
C11	0.0321 (17)	0.0323 (16)	0.057 (2)	−0.0007 (13)	0.0138 (16)	0.0050 (15)
C12	0.0308 (17)	0.0368 (16)	0.0505 (19)	−0.0014 (13)	0.0150 (14)	0.0009 (14)
C13	0.0338 (18)	0.0466 (18)	0.0408 (17)	0.0034 (14)	0.0060 (14)	−0.0029 (15)
C14	0.0350 (19)	0.0513 (19)	0.0442 (18)	0.0081 (15)	0.0129 (15)	−0.0053 (15)
C15	0.0303 (18)	0.0459 (18)	0.0423 (18)	0.0006 (14)	0.0087 (14)	0.0027 (14)
C16	0.040 (2)	0.088 (3)	0.0399 (19)	0.0051 (19)	0.0112 (15)	−0.0084 (18)
C17	0.038 (2)	0.077 (3)	0.051 (2)	0.0028 (18)	0.0194 (16)	−0.0100 (18)
C18	0.0349 (19)	0.055 (2)	0.0395 (18)	0.0039 (15)	0.0073 (14)	0.0052 (15)
C19	0.045 (2)	0.069 (3)	0.071 (3)	0.0093 (19)	0.018 (2)	0.027 (2)
C20	0.043 (2)	0.098 (3)	0.049 (2)	0.006 (2)	0.0063 (18)	−0.004 (2)
C21	0.0263 (17)	0.0460 (18)	0.0414 (17)	0.0026 (13)	0.0028 (13)	0.0007 (14)
C22	0.041 (2)	0.0462 (19)	0.062 (2)	0.0112 (15)	0.0232 (17)	0.0015 (16)
C23	0.042 (2)	0.0393 (18)	0.063 (2)	0.0063 (15)	0.0182 (17)	0.0059 (16)
C24	0.0271 (16)	0.0458 (18)	0.0406 (17)	0.0006 (14)	0.0033 (13)	−0.0029 (15)
C25	0.039 (2)	0.049 (2)	0.052 (2)	0.0141 (15)	0.0130 (16)	0.0012 (16)
C26	0.0374 (19)	0.0458 (19)	0.052 (2)	0.0113 (15)	0.0110 (15)	0.0051 (15)
C27	0.0292 (18)	0.0460 (18)	0.0438 (18)	−0.0028 (14)	0.0025 (14)	−0.0025 (15)

Ag1—N2	2.179 (2)	C8—H8	0.9300
Ag1—N1i	2.186 (2)	C9—C10	1.376 (4)
F1—C19	1.332 (4)	C9—H9	0.9300
F2—C19	1.329 (4)	C10—H10	0.9300
F3—C19	1.342 (4)	C11—C12	1.514 (4)
F4—C20	1.332 (4)	C12—C17	1.380 (4)
F5—C20	1.335 (5)	C12—C13	1.383 (4)
F6—C20	1.341 (4)	C13—C14	1.384 (4)
O1—C11	1.238 (4)	C13—H13	0.9300
O2—C11	1.268 (4)	C14—C15	1.378 (4)
O3—C27	1.212 (4)	C14—H14	0.9300
O4—C27	1.312 (4)	C15—C16	1.380 (4)
O4—H4	0.8200	C15—C18	1.551 (4)
N1—C8	1.330 (4)	C16—C17	1.381 (5)
N1—C9	1.332 (4)	C16—H16	0.9300
N1—Ag1ii	2.186 (2)	C17—H17	0.9300
N2—C3	1.330 (4)	C18—C20	1.532 (5)
N2—C2	1.338 (4)	C18—C19	1.546 (5)
C1—C2	1.365 (4)	C18—C21	1.549 (4)
C1—C5	1.383 (4)	C21—C22	1.382 (4)
C1—H1	0.9300	C21—C26	1.391 (4)
C2—H2	0.9300	C22—C23	1.381 (4)
C3—C4	1.371 (4)	C22—H22	0.9300
C3—H3	0.9300	C23—C24	1.384 (4)
C4—C5	1.388 (4)	C23—H23	0.9300
C4—H4A	0.9300	C24—C25	1.375 (4)
C5—C6	1.485 (4)	C24—C27	1.490 (4)
C6—C7	1.380 (4)	C25—C26	1.383 (4)
C6—C10	1.387 (4)	C25—H25	0.9300
C7—C8	1.373 (4)	C26—H26	0.9300
C7—H7	0.9300
N2—Ag1—N1i	171.36 (9)	C13—C14—H14	119.4
C27—O4—H4	109.5	C14—C15—C16	118.2 (3)
C8—N1—C9	116.6 (3)	C14—C15—C18	118.9 (3)
C8—N1—Ag1ii	124.66 (19)	C16—C15—C18	122.8 (3)
C9—N1—Ag1ii	118.7 (2)	C15—C16—C17	120.5 (3)
C3—N2—C2	116.8 (3)	C15—C16—H16	119.7
C3—N2—Ag1	125.8 (2)	C17—C16—H16	119.7
C2—N2—Ag1	117.01 (19)	C12—C17—C16	121.5 (3)
C2—C1—C5	120.8 (3)	C12—C17—H17	119.2
C2—C1—H1	119.6	C16—C17—H17	119.2
C5—C1—H1	119.6	C20—C18—C19	108.8 (3)
N2—C2—C1	122.8 (3)	C20—C18—C21	106.5 (3)
N2—C2—H2	118.6	C19—C18—C21	111.8 (3)
C1—C2—H2	118.6	C20—C18—C15	113.1 (3)
N2—C3—C4	123.7 (3)	C19—C18—C15	105.4 (3)
N2—C3—H3	118.1	C21—C18—C15	111.3 (2)
C4—C3—H3	118.1	F2—C19—F1	107.3 (3)
C3—C4—C5	119.7 (3)	F2—C19—F3	107.0 (3)
C3—C4—H4A	120.1	F1—C19—F3	106.6 (3)
C5—C4—H4A	120.1	F2—C19—C18	111.2 (3)
C1—C5—C4	116.1 (3)	F1—C19—C18	112.0 (3)
C1—C5—C6	121.7 (3)	F3—C19—C18	112.4 (3)
C4—C5—C6	122.2 (3)	F4—C20—F5	106.8 (3)
C7—C6—C10	116.0 (3)	F4—C20—F6	106.5 (3)
C7—C6—C5	122.6 (3)	F5—C20—F6	106.1 (3)
C10—C6—C5	121.4 (3)	F4—C20—C18	114.1 (3)
C8—C7—C6	120.4 (3)	F5—C20—C18	111.3 (3)
C8—C7—H7	119.8	F6—C20—C18	111.6 (3)
C6—C7—H7	119.8	C22—C21—C26	118.3 (3)
N1—C8—C7	123.5 (3)	C22—C21—C18	117.8 (3)
N1—C8—H8	118.2	C26—C21—C18	123.8 (3)
C7—C8—H8	118.2	C23—C22—C21	121.3 (3)
N1—C9—C10	123.3 (3)	C23—C22—H22	119.4
N1—C9—H9	118.4	C21—C22—H22	119.4
C10—C9—H9	118.4	C22—C23—C24	120.4 (3)
C9—C10—C6	120.2 (3)	C22—C23—H23	119.8
C9—C10—H10	119.9	C24—C23—H23	119.8
C6—C10—H10	119.9	C25—C24—C23	118.3 (3)
O1—C11—O2	123.4 (3)	C25—C24—C27	119.1 (3)
O1—C11—C12	118.5 (3)	C23—C24—C27	122.6 (3)
O2—C11—C12	118.1 (3)	C24—C25—C26	121.8 (3)
C17—C12—C13	117.8 (3)	C24—C25—H25	119.1
C17—C12—C11	119.3 (3)	C26—C25—H25	119.1
C13—C12—C11	123.0 (3)	C25—C26—C21	119.9 (3)
C12—C13—C14	120.8 (3)	C25—C26—H26	120.1
C12—C13—H13	119.6	C21—C26—H26	120.1
C14—C13—H13	119.6	O3—C27—O4	123.7 (3)
C15—C14—C13	121.2 (3)	O3—C27—C24	122.8 (3)
C15—C14—H14	119.4	O4—C27—C24	113.5 (3)
C3—N2—C2—C1	−0.1 (5)	C16—C15—C18—C19	95.2 (4)
Ag1—N2—C2—C1	−174.0 (2)	C14—C15—C18—C21	40.0 (4)
C5—C1—C2—N2	0.2 (5)	C16—C15—C18—C21	−143.4 (3)
C2—N2—C3—C4	−0.5 (5)	C20—C18—C19—F2	−169.7 (3)
Ag1—N2—C3—C4	172.8 (2)	C21—C18—C19—F2	−52.4 (4)
N2—C3—C4—C5	1.0 (5)	C15—C18—C19—F2	68.7 (3)
C2—C1—C5—C4	0.2 (4)	C20—C18—C19—F1	70.2 (4)
C2—C1—C5—C6	−178.4 (3)	C21—C18—C19—F1	−172.5 (3)
C3—C4—C5—C1	−0.8 (4)	C15—C18—C19—F1	−51.4 (4)
C3—C4—C5—C6	177.8 (3)	C20—C18—C19—F3	−49.8 (4)
C1—C5—C6—C7	169.5 (3)	C21—C18—C19—F3	67.5 (4)
C4—C5—C6—C7	−9.0 (4)	C15—C18—C19—F3	−171.4 (3)
C1—C5—C6—C10	−8.0 (4)	C19—C18—C20—F4	−46.5 (4)
C4—C5—C6—C10	173.4 (3)	C21—C18—C20—F4	−167.1 (3)
C10—C6—C7—C8	1.3 (4)	C15—C18—C20—F4	70.3 (4)
C5—C6—C7—C8	−176.3 (3)	C19—C18—C20—F5	−167.4 (3)
C9—N1—C8—C7	−0.6 (5)	C21—C18—C20—F5	72.0 (3)
Ag1ii—N1—C8—C7	−179.9 (2)	C15—C18—C20—F5	−50.6 (4)
C6—C7—C8—N1	−0.3 (5)	C19—C18—C20—F6	74.3 (4)
C8—N1—C9—C10	0.5 (5)	C21—C18—C20—F6	−46.4 (4)
Ag1ii—N1—C9—C10	179.8 (3)	C15—C18—C20—F6	−168.9 (3)
N1—C9—C10—C6	0.6 (6)	C20—C18—C21—C22	−74.4 (4)
C7—C6—C10—C9	−1.4 (5)	C19—C18—C21—C22	166.9 (3)
C5—C6—C10—C9	176.2 (3)	C15—C18—C21—C22	49.3 (4)
O1—C11—C12—C17	−9.6 (4)	C20—C18—C21—C26	103.1 (4)
O2—C11—C12—C17	172.1 (3)	C19—C18—C21—C26	−15.6 (4)
O1—C11—C12—C13	169.8 (3)	C15—C18—C21—C26	−133.2 (3)
O2—C11—C12—C13	−8.4 (4)	C26—C21—C22—C23	−0.5 (5)
C17—C12—C13—C14	−1.1 (5)	C18—C21—C22—C23	177.1 (3)
C11—C12—C13—C14	179.4 (3)	C21—C22—C23—C24	0.5 (5)
C12—C13—C14—C15	0.5 (5)	C22—C23—C24—C25	−0.2 (5)
C13—C14—C15—C16	0.4 (5)	C22—C23—C24—C27	178.2 (3)
C13—C14—C15—C18	177.2 (3)	C23—C24—C25—C26	−0.2 (5)
C14—C15—C16—C17	−0.8 (5)	C27—C24—C25—C26	−178.6 (3)
C18—C15—C16—C17	−177.4 (3)	C24—C25—C26—C21	0.2 (5)
C13—C12—C17—C16	0.8 (5)	C22—C21—C26—C25	0.1 (5)
C11—C12—C17—C16	−179.7 (3)	C18—C21—C26—C25	−177.3 (3)
C15—C16—C17—C12	0.1 (6)	C25—C24—C27—O3	−12.0 (4)
C14—C15—C18—C20	159.8 (3)	C23—C24—C27—O3	169.6 (3)
C16—C15—C18—C20	−23.6 (5)	C25—C24—C27—O4	168.5 (3)
C14—C15—C18—C19	−81.5 (4)	C23—C24—C27—O4	−9.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2iii	0.82	1.72	2.538 (2)	174
C4—H4A···O1iv	0.93	2.52	3.366 (4)	152
C7—H7···O1iv	0.93	2.54	3.297 (4)	138
C8—H8···O3	0.93	2.53	3.312 (4)	142
C9—H9···O2v	0.93	2.48	3.242 (4)	139
C16—H16···F4	0.93	2.35	2.992 (4)	126
C26—H26···F3	0.93	2.33	2.941 (4)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O2i	0.82	1.72	2.538 (2)	174
C4—H4A⋯O1ii	0.93	2.52	3.366 (4)	152
C7—H7⋯O1ii	0.93	2.54	3.297 (4)	138
C8—H8⋯O3	0.93	2.53	3.312 (4)	142
C9—H9⋯O2iii	0.93	2.48	3.242 (4)	139
C16—H16⋯F4	0.93	2.35	2.992 (4)	126
C26—H26⋯F3	0.93	2.33	2.941 (4)	123

Symmetry codes: (i) ; (ii) ; (iii) .