Flunarizinium hydrogen maleate.

In the cation of the title salt {systematic name: 4-[bis-(4-fluoro-phen-yl)meth-yl]-1-[(2E)-3-phenyl-prop-2-en-1-yl]piperazin-1-ium hydrogen maleate}, C26H27F2N2 (+)·C4H3O4 (-), the protonated piperazine ring is in a chair conformation. The dihedral angle between the 4-fluoro-phenyl rings is 68.2 (2)°. An intra-molecular O-H⋯O hydrogen bond occurs in the anion. In the crystal, N-H⋯O, C-H⋯O and C-H⋯F inter-actions are observed, which link the ions into [001] chains.

Related literature

For backgorund to flunarizine, see: Amery (1983 ▶); Holmes et al. (1984 ▶). For related structures, see: Jasinski, Butcher et al. (2010 ▶); Jasinski, Pek et al. (2010 ▶); Kavitha et al. (2013 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C26H27F2N2 +·C4H3O4 −

M = 520.56

Monoclinic,

a = 22.1215 (5) Å

b = 10.8620 (2) Å

c = 11.3215 (2) Å

β = 98.879 (2)°

V = 2687.77 (9) Å3

Z = 4

Cu Kα radiation

μ = 0.79 mm−1

T = 173 K

0.42 × 0.38 × 0.26 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.871, T max = 1.000

17207 measured reflections

5260 independent reflections

4484 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.136

S = 1.03

5260 reflections

344 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813020291/hb7110sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020291/hb7110Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020291/hb7110Isup3.cml

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

C26H27F2N2+·C4H3O4−	F(000) = 1096
Mr = 520.56	Dx = 1.286 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
a = 22.1215 (5) Å	Cell parameters from 6479 reflections
b = 10.8620 (2) Å	θ = 4.0–72.3°
c = 11.3215 (2) Å	µ = 0.79 mm−1
β = 98.879 (2)°	T = 173 K
V = 2687.77 (9) Å3	Irregular, colourless
Z = 4	0.42 × 0.38 × 0.26 mm

Agilent Xcalibur (Eos, Gemini) diffractometer	5260 independent reflections
Radiation source: Enhance (Cu) X-ray Source	4484 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 16.0416 pixels mm-1	θmax = 72.5°, θmin = 4.1°
ω scans	h = −24→27
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −12→13
Tmin = 0.871, Tmax = 1.000	l = −13→8
17207 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.048	w = 1/[σ2(Fo2) + (0.0702P)2 + 0.7817P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.136	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.52 e Å−3
5260 reflections	Δρmin = −0.22 e Å−3
344 parameters	Extinction correction: SHELXL2012 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0021 (2)
Primary atom site location: structure-invariant direct methods

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
F1	0.87928 (7)	−0.24891 (14)	0.47740 (13)	0.0848 (5)
F2	0.98166 (6)	0.06251 (14)	1.26090 (10)	0.0727 (4)
N1	0.68788 (6)	0.32014 (12)	0.73573 (11)	0.0319 (3)
H1	0.7039	0.3791	0.6926	0.038*
N2	0.79790 (5)	0.17520 (11)	0.79037 (10)	0.0280 (3)
C1	0.72463 (8)	0.31929 (15)	0.85715 (13)	0.0363 (4)
H1A	0.7093	0.2563	0.9055	0.044*
H1B	0.7211	0.3983	0.8954	0.044*
C2	0.79108 (7)	0.29391 (14)	0.84796 (13)	0.0332 (3)
H2A	0.8066	0.3588	0.8021	0.040*
H2B	0.8150	0.2938	0.9274	0.040*
C3	0.76221 (7)	0.17749 (14)	0.67002 (12)	0.0306 (3)
H3A	0.7669	0.0997	0.6303	0.037*
H3B	0.7773	0.2425	0.6236	0.037*
C4	0.69533 (7)	0.19923 (14)	0.67663 (13)	0.0330 (3)
H4A	0.6720	0.1992	0.5967	0.040*
H4B	0.6799	0.1336	0.7218	0.040*
C5	0.62138 (8)	0.35276 (17)	0.73677 (15)	0.0411 (4)
H5A	0.5996	0.2815	0.7601	0.049*
H5B	0.6185	0.4179	0.7942	0.049*
C6	0.59335 (8)	0.39422 (18)	0.61479 (16)	0.0445 (4)
H6	0.6034	0.4726	0.5911	0.053*
C7	0.55601 (8)	0.32949 (17)	0.53891 (18)	0.0470 (4)
H7	0.5435	0.2535	0.5645	0.056*
C8	0.53185 (8)	0.36771 (17)	0.41482 (16)	0.0433 (4)
C9	0.47868 (9)	0.31385 (18)	0.35792 (19)	0.0496 (4)
H9	0.4588	0.2557	0.3984	0.059*
C10	0.45461 (9)	0.3450 (2)	0.2417 (2)	0.0579 (5)
H10	0.4186	0.3083	0.2051	0.069*
C11	0.48338 (10)	0.4293 (2)	0.18018 (18)	0.0564 (5)
H11	0.4669	0.4505	0.1023	0.068*
C12	0.53710 (10)	0.48277 (19)	0.23452 (19)	0.0565 (5)
H12	0.5573	0.5392	0.1927	0.068*
C13	0.56108 (9)	0.45259 (18)	0.35134 (18)	0.0501 (4)
H13	0.5971	0.4896	0.3876	0.060*
C14	0.86369 (7)	0.14809 (13)	0.79043 (13)	0.0287 (3)
H14	0.8825	0.2201	0.7587	0.034*
C15	0.87072 (6)	0.03898 (14)	0.70972 (13)	0.0292 (3)
C16	0.84983 (8)	−0.07710 (15)	0.73468 (15)	0.0378 (4)
H16	0.8335	−0.0896	0.8046	0.045*
C17	0.85290 (9)	−0.17466 (17)	0.65714 (18)	0.0486 (4)
H17	0.8386	−0.2523	0.6738	0.058*
C18	0.87752 (9)	−0.15360 (19)	0.55528 (18)	0.0528 (5)
C19	0.90001 (9)	−0.0420 (2)	0.52802 (16)	0.0502 (5)
H19	0.9173	−0.0313	0.4589	0.060*
C20	0.89645 (7)	0.05539 (16)	0.60644 (14)	0.0377 (4)
H20	0.9115	0.1323	0.5895	0.045*
C21	0.89532 (7)	0.12623 (13)	0.91779 (13)	0.0298 (3)
C22	0.95568 (7)	0.16234 (15)	0.95284 (15)	0.0384 (4)
H22	0.9765	0.2017	0.8983	0.046*
C23	0.98534 (8)	0.14033 (19)	1.06856 (17)	0.0490 (5)
H23	1.0258	0.1644	1.0919	0.059*
C24	0.95369 (9)	0.08262 (18)	1.14703 (15)	0.0468 (4)
C25	0.89418 (8)	0.04536 (16)	1.11636 (15)	0.0419 (4)
H25	0.8738	0.0058	1.1716	0.050*
C26	0.86487 (7)	0.06801 (15)	1.00075 (13)	0.0345 (3)
H26	0.8244	0.0439	0.9786	0.041*
O1S	0.67312 (8)	0.83923 (13)	0.66302 (12)	0.0604 (4)
H1S	0.6848	0.7679	0.6735	0.091*
O2S	0.65899 (8)	0.97228 (12)	0.51543 (12)	0.0589 (4)
O3S	0.72834 (6)	0.47153 (13)	0.57335 (13)	0.0561 (4)
O4S	0.70541 (8)	0.62367 (13)	0.68757 (11)	0.0600 (4)
C1S	0.67577 (8)	0.87144 (16)	0.55309 (15)	0.0411 (4)
C2S	0.70000 (8)	0.78300 (16)	0.47107 (14)	0.0400 (4)
H2S	0.7043	0.8161	0.3971	0.048*
C3S	0.71654 (8)	0.66586 (16)	0.48435 (15)	0.0406 (4)
H3S	0.7298	0.6303	0.4182	0.049*
C4S	0.71709 (8)	0.58175 (17)	0.58972 (16)	0.0410 (4)

	U11	U22	U33	U12	U13	U23
F1	0.0965 (11)	0.0745 (9)	0.0831 (10)	0.0137 (8)	0.0126 (8)	−0.0504 (8)
F2	0.0663 (8)	0.1044 (11)	0.0390 (6)	0.0294 (7)	−0.0186 (5)	−0.0032 (6)
N1	0.0355 (7)	0.0320 (7)	0.0284 (6)	0.0097 (5)	0.0059 (5)	0.0009 (5)
N2	0.0315 (6)	0.0274 (6)	0.0241 (6)	0.0060 (5)	0.0014 (5)	−0.0013 (5)
C1	0.0445 (9)	0.0383 (8)	0.0256 (7)	0.0111 (7)	0.0034 (6)	−0.0052 (6)
C2	0.0402 (8)	0.0310 (8)	0.0271 (7)	0.0067 (6)	0.0008 (6)	−0.0050 (6)
C3	0.0352 (8)	0.0316 (7)	0.0241 (7)	0.0072 (6)	0.0020 (6)	−0.0041 (5)
C4	0.0351 (8)	0.0330 (8)	0.0297 (8)	0.0076 (6)	0.0010 (6)	−0.0045 (6)
C5	0.0374 (9)	0.0461 (9)	0.0414 (9)	0.0136 (7)	0.0108 (7)	−0.0006 (7)
C6	0.0380 (9)	0.0456 (10)	0.0499 (10)	0.0139 (7)	0.0062 (8)	−0.0011 (8)
C7	0.0431 (10)	0.0419 (10)	0.0575 (11)	0.0018 (7)	0.0128 (8)	0.0039 (8)
C8	0.0402 (9)	0.0437 (9)	0.0462 (10)	0.0112 (7)	0.0071 (7)	−0.0011 (7)
C9	0.0452 (10)	0.0438 (10)	0.0606 (12)	0.0033 (8)	0.0110 (9)	−0.0039 (8)
C10	0.0440 (10)	0.0640 (13)	0.0622 (12)	0.0092 (9)	−0.0027 (9)	−0.0222 (10)
C11	0.0629 (13)	0.0612 (13)	0.0429 (10)	0.0279 (10)	0.0016 (9)	−0.0051 (9)
C12	0.0714 (14)	0.0420 (10)	0.0583 (12)	0.0101 (9)	0.0170 (10)	0.0076 (9)
C13	0.0463 (10)	0.0471 (10)	0.0557 (11)	−0.0010 (8)	0.0040 (8)	−0.0049 (8)
C14	0.0313 (7)	0.0256 (7)	0.0296 (7)	0.0016 (5)	0.0058 (6)	0.0018 (5)
C15	0.0284 (7)	0.0304 (7)	0.0276 (7)	0.0068 (6)	0.0003 (5)	0.0003 (6)
C16	0.0425 (9)	0.0316 (8)	0.0394 (8)	0.0040 (7)	0.0070 (7)	−0.0025 (6)
C17	0.0504 (10)	0.0337 (9)	0.0591 (11)	0.0052 (7)	0.0007 (9)	−0.0101 (8)
C18	0.0516 (11)	0.0530 (11)	0.0509 (11)	0.0156 (9)	−0.0015 (8)	−0.0254 (9)
C19	0.0497 (10)	0.0682 (13)	0.0337 (9)	0.0147 (9)	0.0092 (7)	−0.0096 (8)
C20	0.0370 (8)	0.0439 (9)	0.0324 (8)	0.0065 (7)	0.0054 (6)	0.0021 (7)
C21	0.0318 (7)	0.0256 (7)	0.0311 (7)	0.0045 (6)	0.0018 (6)	−0.0035 (6)
C22	0.0319 (8)	0.0391 (9)	0.0434 (9)	0.0023 (6)	0.0040 (7)	−0.0071 (7)
C23	0.0321 (8)	0.0586 (11)	0.0520 (10)	0.0084 (8)	−0.0072 (8)	−0.0149 (9)
C24	0.0474 (10)	0.0564 (11)	0.0319 (8)	0.0223 (8)	−0.0090 (7)	−0.0075 (7)
C25	0.0505 (10)	0.0432 (9)	0.0310 (8)	0.0126 (7)	0.0034 (7)	0.0023 (7)
C26	0.0358 (8)	0.0350 (8)	0.0313 (8)	0.0020 (6)	0.0003 (6)	0.0007 (6)
O1S	0.0998 (12)	0.0472 (8)	0.0383 (7)	−0.0015 (7)	0.0241 (7)	−0.0015 (6)
O2S	0.0891 (11)	0.0335 (7)	0.0551 (8)	−0.0014 (7)	0.0143 (7)	0.0013 (6)
O3S	0.0599 (8)	0.0490 (8)	0.0651 (9)	0.0202 (6)	0.0275 (7)	0.0206 (6)
O4S	0.0962 (12)	0.0536 (8)	0.0317 (6)	0.0022 (8)	0.0142 (7)	0.0111 (6)
C1S	0.0502 (10)	0.0368 (9)	0.0362 (8)	−0.0123 (7)	0.0061 (7)	−0.0007 (7)
C2S	0.0497 (10)	0.0432 (9)	0.0278 (8)	−0.0045 (7)	0.0084 (7)	0.0065 (7)
C3S	0.0455 (9)	0.0461 (10)	0.0323 (8)	0.0034 (7)	0.0122 (7)	0.0056 (7)
C4S	0.0361 (8)	0.0469 (10)	0.0411 (9)	0.0041 (7)	0.0092 (7)	0.0126 (7)

F1—C18	1.364 (2)	C12—C13	1.386 (3)
F2—C24	1.3589 (19)	C13—H13	0.9300
N1—H1	0.9101	C14—H14	0.9800
N1—C1	1.4851 (19)	C14—C15	1.519 (2)
N1—C4	1.4945 (18)	C14—C21	1.521 (2)
N1—C5	1.5150 (19)	C15—C16	1.387 (2)
N2—C2	1.4632 (18)	C15—C20	1.389 (2)
N2—C3	1.4657 (17)	C16—H16	0.9300
N2—C14	1.4848 (18)	C16—C17	1.384 (2)
C1—H1A	0.9700	C17—H17	0.9300
C1—H1B	0.9700	C17—C18	1.368 (3)
C1—C2	1.515 (2)	C18—C19	1.364 (3)
C2—H2A	0.9700	C19—H19	0.9300
C2—H2B	0.9700	C19—C20	1.391 (2)
C3—H3A	0.9700	C20—H20	0.9300
C3—H3B	0.9700	C21—C22	1.390 (2)
C3—C4	1.512 (2)	C21—C26	1.390 (2)
C4—H4A	0.9700	C22—H22	0.9300
C4—H4B	0.9700	C22—C23	1.392 (2)
C5—H5A	0.9700	C23—H23	0.9300
C5—H5B	0.9700	C23—C24	1.365 (3)
C5—C6	1.493 (2)	C24—C25	1.370 (3)
C6—H6	0.9300	C25—H25	0.9300
C6—C7	1.302 (3)	C25—C26	1.390 (2)
C7—H7	0.9300	C26—H26	0.9300
C7—C8	1.483 (3)	O1S—H1S	0.8199
C8—C9	1.381 (3)	O1S—C1S	1.303 (2)
C8—C13	1.389 (3)	O2S—C1S	1.213 (2)
C9—H9	0.9300	O3S—C4S	1.243 (2)
C9—C10	1.383 (3)	O4S—C4S	1.261 (2)
C10—H10	0.9300	C1S—C2S	1.492 (2)
C10—C11	1.366 (3)	C2S—H2S	0.9300
C11—H11	0.9300	C2S—C3S	1.326 (2)
C11—C12	1.379 (3)	C3S—H3S	0.9300
C12—H12	0.9300	C3S—C4S	1.501 (2)
C1—N1—H1	107.4	C13—C12—H12	119.9
C1—N1—C4	109.06 (11)	C8—C13—H13	119.6
C1—N1—C5	112.81 (12)	C12—C13—C8	120.71 (19)
C4—N1—H1	107.4	C12—C13—H13	119.6
C4—N1—C5	112.53 (13)	N2—C14—H14	108.3
C5—N1—H1	107.4	N2—C14—C15	110.23 (12)
C2—N2—C3	108.75 (11)	N2—C14—C21	109.81 (11)
C2—N2—C14	110.06 (12)	C15—C14—H14	108.3
C3—N2—C14	113.02 (11)	C15—C14—C21	111.94 (11)
N1—C1—H1A	109.7	C21—C14—H14	108.3
N1—C1—H1B	109.7	C16—C15—C14	121.22 (13)
N1—C1—C2	109.63 (12)	C16—C15—C20	118.75 (14)
H1A—C1—H1B	108.2	C20—C15—C14	119.98 (14)
C2—C1—H1A	109.7	C15—C16—H16	119.5
C2—C1—H1B	109.7	C17—C16—C15	121.07 (16)
N2—C2—C1	111.03 (13)	C17—C16—H16	119.5
N2—C2—H2A	109.4	C16—C17—H17	120.9
N2—C2—H2B	109.4	C18—C17—C16	118.12 (18)
C1—C2—H2A	109.4	C18—C17—H17	120.9
C1—C2—H2B	109.4	F1—C18—C17	118.2 (2)
H2A—C2—H2B	108.0	C19—C18—F1	118.71 (19)
N2—C3—H3A	109.6	C19—C18—C17	123.09 (16)
N2—C3—H3B	109.6	C18—C19—H19	120.9
N2—C3—C4	110.34 (11)	C18—C19—C20	118.22 (17)
H3A—C3—H3B	108.1	C20—C19—H19	120.9
C4—C3—H3A	109.6	C15—C20—C19	120.71 (17)
C4—C3—H3B	109.6	C15—C20—H20	119.6
N1—C4—C3	109.62 (12)	C19—C20—H20	119.6
N1—C4—H4A	109.7	C22—C21—C14	120.52 (14)
N1—C4—H4B	109.7	C26—C21—C14	120.78 (13)
C3—C4—H4A	109.7	C26—C21—C22	118.69 (14)
C3—C4—H4B	109.7	C21—C22—H22	119.6
H4A—C4—H4B	108.2	C21—C22—C23	120.84 (16)
N1—C5—H5A	109.8	C23—C22—H22	119.6
N1—C5—H5B	109.8	C22—C23—H23	120.8
H5A—C5—H5B	108.3	C24—C23—C22	118.47 (16)
C6—C5—N1	109.17 (13)	C24—C23—H23	120.8
C6—C5—H5A	109.8	F2—C24—C23	119.13 (17)
C6—C5—H5B	109.8	F2—C24—C25	118.18 (18)
C5—C6—H6	117.4	C23—C24—C25	122.68 (16)
C7—C6—C5	125.30 (19)	C24—C25—H25	120.8
C7—C6—H6	117.4	C24—C25—C26	118.47 (17)
C6—C7—H7	117.5	C26—C25—H25	120.8
C6—C7—C8	124.96 (18)	C21—C26—C25	120.85 (15)
C8—C7—H7	117.5	C21—C26—H26	119.6
C9—C8—C7	118.67 (18)	C25—C26—H26	119.6
C9—C8—C13	118.10 (18)	C1S—O1S—H1S	109.4
C13—C8—C7	123.21 (17)	O1S—C1S—C2S	119.68 (16)
C8—C9—H9	119.5	O2S—C1S—O1S	121.46 (17)
C8—C9—C10	121.01 (19)	O2S—C1S—C2S	118.86 (16)
C10—C9—H9	119.5	C1S—C2S—H2S	114.1
C9—C10—H10	119.7	C3S—C2S—C1S	131.80 (15)
C11—C10—C9	120.5 (2)	C3S—C2S—H2S	114.1
C11—C10—H10	119.7	C2S—C3S—H3S	115.0
C10—C11—H11	120.3	C2S—C3S—C4S	129.96 (16)
C10—C11—C12	119.48 (19)	C4S—C3S—H3S	115.0
C12—C11—H11	120.3	O3S—C4S—O4S	123.50 (16)
C11—C12—H12	119.9	O3S—C4S—C3S	116.43 (16)
C11—C12—C13	120.2 (2)	O4S—C4S—C3S	120.06 (16)
F1—C18—C19—C20	178.26 (17)	C13—C8—C9—C10	−1.1 (3)
F2—C24—C25—C26	178.65 (15)	C14—N2—C2—C1	−175.83 (12)
N1—C1—C2—N2	−59.35 (16)	C14—N2—C3—C4	177.21 (12)
N1—C5—C6—C7	104.8 (2)	C14—C15—C16—C17	175.99 (15)
N2—C3—C4—N1	60.33 (16)	C14—C15—C20—C19	−176.28 (15)
N2—C14—C15—C16	−63.63 (17)	C14—C21—C22—C23	−178.65 (14)
N2—C14—C15—C20	113.99 (15)	C14—C21—C26—C25	178.47 (14)
N2—C14—C21—C22	−145.85 (14)	C15—C14—C21—C22	91.37 (16)
N2—C14—C21—C26	35.24 (18)	C15—C14—C21—C26	−87.53 (17)
C1—N1—C4—C3	−58.52 (16)	C15—C16—C17—C18	0.4 (3)
C1—N1—C5—C6	160.42 (14)	C16—C15—C20—C19	1.4 (2)
C2—N2—C3—C4	−60.26 (16)	C16—C17—C18—F1	−178.50 (17)
C2—N2—C14—C15	−168.65 (11)	C16—C17—C18—C19	1.2 (3)
C2—N2—C14—C21	67.58 (14)	C17—C18—C19—C20	−1.4 (3)
C3—N2—C2—C1	59.86 (15)	C18—C19—C20—C15	0.1 (3)
C3—N2—C14—C15	−46.84 (15)	C20—C15—C16—C17	−1.7 (2)
C3—N2—C14—C21	−170.62 (12)	C21—C14—C15—C16	58.90 (18)
C4—N1—C1—C2	57.71 (16)	C21—C14—C15—C20	−123.48 (15)
C4—N1—C5—C6	−75.65 (17)	C21—C22—C23—C24	−0.1 (3)
C5—N1—C1—C2	−176.47 (13)	C22—C21—C26—C25	−0.5 (2)
C5—N1—C4—C3	175.51 (12)	C22—C23—C24—F2	−178.81 (15)
C5—C6—C7—C8	−175.39 (15)	C22—C23—C24—C25	0.2 (3)
C6—C7—C8—C9	−158.61 (19)	C23—C24—C25—C26	−0.4 (3)
C6—C7—C8—C13	23.4 (3)	C24—C25—C26—C21	0.5 (2)
C7—C8—C9—C10	−179.18 (17)	C26—C21—C22—C23	0.3 (2)
C7—C8—C13—C12	178.51 (17)	O1S—C1S—C2S—C3S	6.3 (3)
C8—C9—C10—C11	0.6 (3)	O2S—C1S—C2S—C3S	−173.7 (2)
C9—C8—C13—C12	0.5 (3)	C1S—C2S—C3S—C4S	−0.9 (3)
C9—C10—C11—C12	0.5 (3)	C2S—C3S—C4S—O3S	172.11 (19)
C10—C11—C12—C13	−1.1 (3)	C2S—C3S—C4S—O4S	−6.6 (3)
C11—C12—C13—C8	0.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1S—H1S···O4S	0.82	1.63	2.451 (2)	177
N1—H1···O3S	0.91	1.83	2.7190 (18)	165
C1—H1B···O2Si	0.97	2.51	3.354 (2)	146
C26—H26···O3Sii	0.93	2.53	3.278 (2)	138
C2S—H2S···O4Siii	0.93	2.46	3.386 (2)	171
C23—H23···F1iv	0.93	2.53	3.342 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1S—H1S⋯O4S	0.82	1.63	2.451 (2)	177
N1—H1⋯O3S	0.91	1.83	2.7190 (18)	165
C1—H1B⋯O2S i	0.97	2.51	3.354 (2)	146
C26—H26⋯O3S ii	0.93	2.53	3.278 (2)	138
C2S—H2S⋯O4S iii	0.93	2.46	3.386 (2)	171
C23—H23⋯F1iv	0.93	2.53	3.342 (2)	145

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