N-[Bis(dimethyl-amino)-methyl-idene]-2-[(triphenyl-meth-yl)sulfan-yl]ethanaminium hexa-fluoro-phosphate.

The mol-ecular structure of the title compound, C(26)H(32)N(3)S(+)·PF(6) (-), shows a protonated guanidyl group bridged by an ethyl-ene linker with a tritylsulfanyl unit. The guanidinium (gua) unit displays charge delocalization over the three N-C(gua) bonds. The N-C-C-S group shows a folded nonplanar conformation with a torsion angle of 158.4 (1)°. In the crystal, the cation and anion are linked by an N-H⋯F inter-action.

Related literature

For the synthesis, see: Herres-Pawlis et al. (2005 ▶). For related structures, see: Flörke et al. (2006 ▶); Neuba et al. (2007c ▶); Pruszynski et al. (1992 ▶). For related chemistry literature, see: Börner et al. (2007 ▶, 2009 ▶); Galezowski et al. (1994 ▶); Harmjanz (1997 ▶); Herres et al. (2005 ▶); Herres-Pawlis et al. (2009 ▶); Neuba (2009 ▶); Neuba et al. (2007a ▶,b ▶, 2008a ▶,b ▶, 2010 ▶, 2011 ▶); Peters et al. (2008 ▶); Pohl et al. (2000 ▶); Raab et al. (2003 ▶); Schneider (2000 ▶); Waden (1999 ▶); Wittman (1999 ▶); Wittmann et al. (2001 ▶).

Experimental

Crystal data

C26H32N3S+·PF6 −

M = 563.58

Triclinic,

a = 9.0111 (14) Å

b = 9.1376 (15) Å

c = 17.564 (3) Å

α = 96.532 (3)°

β = 100.225 (4)°

γ = 108.053 (3)°

V = 1331.0 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 120 K

0.33 × 0.30 × 0.26 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.924, T max = 0.939

11922 measured reflections

6281 independent reflections

4547 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.104

S = 0.96

6281 reflections

338 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.42 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014929/bt5504sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014929/bt5504Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811014929/bt5504Isup3.cml

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

C26H32N3S+·PF6−	Z = 2
Mr = 563.58	F(000) = 588
Triclinic, P1	Dx = 1.406 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0111 (14) Å	Cell parameters from 786 reflections
b = 9.1376 (15) Å	θ = 2.4–27.9°
c = 17.564 (3) Å	µ = 0.25 mm−1
α = 96.532 (3)°	T = 120 K
β = 100.225 (4)°	Block, colourless
γ = 108.053 (3)°	0.33 × 0.30 × 0.26 mm
V = 1331.0 (4) Å3

Bruker SMART APEX diffractometer	6281 independent reflections
Radiation source: sealed tube	4547 reflections with I > 2σ(I)
graphite	Rint = 0.060
φ and ω scans	θmax = 27.9°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→10
Tmin = 0.924, Tmax = 0.939	k = −12→11
11922 measured reflections	l = −23→20

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)] = 0.047	Hydrogen site location: difference Fourier map
wR(F2) = 0.104	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0445P)2] where P = (Fo2 + 2Fc2)/3
6281 reflections	(Δ/σ)max < 0.001
338 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.42 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
S1	0.77994 (6)	0.61888 (5)	0.29140 (3)	0.02002 (12)
N1	0.6327 (2)	0.89606 (18)	0.43688 (9)	0.0242 (4)
H1A	0.6289	0.8850	0.4857	0.029*
N2	0.7383 (2)	1.16512 (18)	0.47245 (9)	0.0253 (4)
N3	0.5695 (2)	1.05179 (18)	0.34970 (9)	0.0252 (4)
C1	0.6470 (2)	1.0380 (2)	0.41911 (10)	0.0211 (4)
C2	0.7029 (3)	1.3121 (2)	0.47981 (13)	0.0378 (6)
H2A	0.7840	1.3922	0.4625	0.057*
H2B	0.7042	1.3471	0.5348	0.057*
H2C	0.5969	1.2948	0.4470	0.057*
C3	0.8710 (3)	1.1626 (3)	0.53285 (12)	0.0338 (5)
H3A	0.8341	1.1432	0.5812	0.051*
H3B	0.9578	1.2636	0.5434	0.051*
H3C	0.9102	1.0792	0.5145	0.051*
C4	0.6343 (3)	1.1837 (3)	0.31065 (13)	0.0407 (6)
H4A	0.5737	1.2556	0.3145	0.061*
H4B	0.6252	1.1443	0.2551	0.061*
H4C	0.7473	1.2390	0.3362	0.061*
C5	0.4191 (3)	0.9342 (3)	0.30549 (12)	0.0350 (5)
H5A	0.4396	0.8717	0.2619	0.052*
H5B	0.3447	0.9862	0.2845	0.052*
H5C	0.3720	0.8657	0.3403	0.052*
C6	0.6227 (2)	0.7568 (2)	0.38190 (11)	0.0245 (4)
H6A	0.5129	0.7109	0.3485	0.029*
H6B	0.6430	0.6775	0.4124	0.029*
C7	0.7419 (2)	0.7943 (2)	0.32952 (11)	0.0207 (4)
H7A	0.8437	0.8738	0.3601	0.025*
H7B	0.6989	0.8384	0.2852	0.025*
C8	0.7037 (2)	0.5855 (2)	0.18294 (10)	0.0173 (4)
C11	0.6980 (2)	0.4160 (2)	0.15696 (10)	0.0177 (4)
C12	0.8390 (2)	0.3816 (2)	0.17641 (11)	0.0226 (4)
H12A	0.9333	0.4611	0.2068	0.027*
C13	0.8442 (2)	0.2340 (2)	0.15229 (12)	0.0269 (4)
H13A	0.9412	0.2127	0.1664	0.032*
C14	0.7079 (3)	0.1177 (2)	0.10767 (11)	0.0270 (5)
H14A	0.7109	0.0164	0.0906	0.032*
C15	0.5672 (3)	0.1497 (2)	0.08807 (11)	0.0266 (4)
H15A	0.4732	0.0697	0.0578	0.032*
C16	0.5622 (2)	0.2984 (2)	0.11234 (11)	0.0220 (4)
H16A	0.4649	0.3192	0.0982	0.026*
C21	0.5359 (2)	0.5994 (2)	0.16573 (10)	0.0172 (4)
C22	0.4204 (2)	0.5180 (2)	0.20308 (10)	0.0206 (4)
H22A	0.4475	0.4567	0.2399	0.025*
C23	0.2669 (2)	0.5248 (2)	0.18760 (11)	0.0230 (4)
H23A	0.1900	0.4685	0.2138	0.028*
C24	0.2246 (2)	0.6135 (2)	0.13396 (11)	0.0237 (4)
H24A	0.1192	0.6181	0.1233	0.028*
C25	0.3372 (2)	0.6948 (2)	0.09638 (11)	0.0235 (4)
H25A	0.3092	0.7558	0.0596	0.028*
C26	0.4920 (2)	0.6881 (2)	0.11204 (11)	0.0208 (4)
H26A	0.5686	0.7448	0.0858	0.025*
C31	0.8208 (2)	0.6940 (2)	0.14281 (10)	0.0183 (4)
C32	0.8071 (2)	0.6503 (2)	0.06202 (11)	0.0231 (4)
H32A	0.7257	0.5565	0.0338	0.028*
C33	0.9100 (2)	0.7415 (2)	0.02285 (11)	0.0268 (4)
H33A	0.8989	0.7100	−0.0319	0.032*
C34	1.0294 (2)	0.8785 (2)	0.06290 (12)	0.0259 (4)
H34A	1.1011	0.9406	0.0361	0.031*
C35	1.0432 (2)	0.9240 (2)	0.14238 (12)	0.0252 (4)
H35A	1.1240	1.0185	0.1701	0.030*
C36	0.9401 (2)	0.8329 (2)	0.18186 (11)	0.0216 (4)
H36A	0.9512	0.8658	0.2365	0.026*
P1	0.19146 (7)	0.27386 (6)	0.37421 (3)	0.02543 (13)
F1	0.02793 (18)	0.13314 (18)	0.35865 (10)	0.0699 (5)
F2	0.20703 (19)	0.22909 (16)	0.28687 (7)	0.0526 (4)
F3	0.35707 (17)	0.41217 (16)	0.39103 (9)	0.0547 (4)
F4	0.10033 (18)	0.38923 (16)	0.34893 (8)	0.0531 (4)
F5	0.18070 (19)	0.31694 (17)	0.46304 (8)	0.0524 (4)
F6	0.28644 (18)	0.15713 (16)	0.40077 (7)	0.0472 (4)

	U11	U22	U33	U12	U13	U23
S1	0.0229 (3)	0.0197 (2)	0.0182 (2)	0.0101 (2)	0.00173 (19)	0.00234 (17)
N1	0.0361 (10)	0.0218 (8)	0.0170 (8)	0.0095 (8)	0.0118 (7)	0.0047 (6)
N2	0.0275 (10)	0.0227 (8)	0.0245 (9)	0.0083 (7)	0.0052 (7)	0.0003 (7)
N3	0.0312 (10)	0.0246 (9)	0.0219 (8)	0.0126 (8)	0.0058 (7)	0.0043 (7)
C1	0.0222 (11)	0.0251 (10)	0.0198 (9)	0.0107 (8)	0.0100 (8)	0.0032 (8)
C2	0.0447 (15)	0.0216 (11)	0.0446 (14)	0.0110 (10)	0.0088 (11)	−0.0019 (9)
C3	0.0299 (12)	0.0375 (12)	0.0279 (11)	0.0083 (10)	0.0006 (10)	−0.0007 (9)
C4	0.0584 (17)	0.0377 (13)	0.0347 (12)	0.0214 (12)	0.0157 (12)	0.0186 (10)
C5	0.0346 (13)	0.0395 (13)	0.0291 (11)	0.0195 (11)	−0.0029 (10)	−0.0047 (9)
C6	0.0339 (12)	0.0191 (9)	0.0225 (10)	0.0103 (9)	0.0093 (9)	0.0031 (7)
C7	0.0222 (10)	0.0161 (9)	0.0232 (10)	0.0066 (8)	0.0045 (8)	0.0026 (7)
C8	0.0179 (10)	0.0160 (9)	0.0159 (9)	0.0045 (8)	0.0018 (7)	0.0019 (7)
C11	0.0207 (10)	0.0170 (9)	0.0168 (9)	0.0068 (8)	0.0064 (8)	0.0045 (7)
C12	0.0195 (10)	0.0198 (9)	0.0273 (10)	0.0057 (8)	0.0054 (8)	0.0022 (8)
C13	0.0281 (12)	0.0250 (10)	0.0328 (11)	0.0137 (9)	0.0100 (9)	0.0067 (8)
C14	0.0374 (13)	0.0169 (9)	0.0292 (11)	0.0108 (9)	0.0122 (10)	0.0018 (8)
C15	0.0295 (12)	0.0208 (10)	0.0234 (10)	0.0012 (9)	0.0066 (9)	−0.0008 (8)
C16	0.0215 (11)	0.0224 (10)	0.0204 (9)	0.0069 (8)	0.0026 (8)	0.0020 (7)
C21	0.0168 (10)	0.0149 (8)	0.0173 (9)	0.0054 (7)	−0.0001 (7)	−0.0014 (7)
C22	0.0227 (11)	0.0200 (9)	0.0211 (10)	0.0091 (8)	0.0044 (8)	0.0065 (7)
C23	0.0192 (10)	0.0227 (10)	0.0270 (10)	0.0055 (8)	0.0068 (8)	0.0061 (8)
C24	0.0173 (10)	0.0258 (10)	0.0287 (11)	0.0100 (8)	0.0033 (8)	0.0033 (8)
C25	0.0248 (11)	0.0229 (10)	0.0250 (10)	0.0115 (9)	0.0029 (9)	0.0077 (8)
C26	0.0210 (10)	0.0191 (9)	0.0230 (10)	0.0070 (8)	0.0052 (8)	0.0057 (7)
C31	0.0173 (10)	0.0179 (9)	0.0228 (9)	0.0094 (8)	0.0046 (8)	0.0052 (7)
C32	0.0210 (10)	0.0216 (9)	0.0246 (10)	0.0057 (8)	0.0023 (8)	0.0044 (8)
C33	0.0290 (12)	0.0313 (11)	0.0226 (10)	0.0114 (10)	0.0068 (9)	0.0098 (8)
C34	0.0246 (11)	0.0262 (10)	0.0336 (11)	0.0122 (9)	0.0110 (9)	0.0155 (9)
C35	0.0190 (10)	0.0175 (9)	0.0375 (12)	0.0047 (8)	0.0041 (9)	0.0061 (8)
C36	0.0197 (10)	0.0200 (9)	0.0253 (10)	0.0078 (8)	0.0044 (8)	0.0033 (8)
P1	0.0307 (3)	0.0207 (3)	0.0231 (3)	0.0066 (2)	0.0047 (2)	0.0047 (2)
F1	0.0451 (10)	0.0428 (9)	0.0994 (13)	−0.0102 (7)	0.0113 (9)	0.0027 (9)
F2	0.0916 (12)	0.0495 (9)	0.0248 (7)	0.0340 (9)	0.0148 (7)	0.0079 (6)
F3	0.0403 (9)	0.0380 (8)	0.0720 (10)	−0.0026 (7)	0.0121 (8)	0.0015 (7)
F4	0.0661 (11)	0.0509 (9)	0.0512 (9)	0.0377 (8)	0.0019 (8)	0.0112 (7)
F5	0.0803 (11)	0.0580 (9)	0.0337 (7)	0.0362 (9)	0.0256 (7)	0.0098 (6)
F6	0.0765 (11)	0.0483 (8)	0.0350 (7)	0.0411 (8)	0.0162 (7)	0.0173 (6)

S1—C7	1.8202 (17)	C13—C14	1.383 (3)
S1—C8	1.8620 (18)	C13—H13A	0.9500
N1—C1	1.341 (2)	C14—C15	1.381 (3)
N1—C6	1.476 (2)	C14—H14A	0.9500
N1—H1A	0.8800	C15—C16	1.394 (2)
N2—C1	1.338 (2)	C15—H15A	0.9500
N2—C3	1.459 (3)	C16—H16A	0.9500
N2—C2	1.470 (2)	C21—C22	1.393 (3)
N3—C1	1.333 (2)	C21—C26	1.394 (2)
N3—C5	1.459 (3)	C22—C23	1.384 (3)
N3—C4	1.469 (3)	C22—H22A	0.9500
C2—H2A	0.9800	C23—C24	1.388 (3)
C2—H2B	0.9800	C23—H23A	0.9500
C2—H2C	0.9800	C24—C25	1.378 (3)
C3—H3A	0.9800	C24—H24A	0.9500
C3—H3B	0.9800	C25—C26	1.395 (3)
C3—H3C	0.9800	C25—H25A	0.9500
C4—H4A	0.9800	C26—H26A	0.9500
C4—H4B	0.9800	C31—C36	1.390 (2)
C4—H4C	0.9800	C31—C32	1.402 (2)
C5—H5A	0.9800	C32—C33	1.381 (3)
C5—H5B	0.9800	C32—H32A	0.9500
C5—H5C	0.9800	C33—C34	1.384 (3)
C6—C7	1.521 (3)	C33—H33A	0.9500
C6—H6A	0.9900	C34—C35	1.383 (3)
C6—H6B	0.9900	C34—H34A	0.9500
C7—H7A	0.9900	C35—C36	1.385 (3)
C7—H7B	0.9900	C35—H35A	0.9500
C8—C21	1.537 (2)	C36—H36A	0.9500
C8—C31	1.538 (2)	P1—F4	1.5801 (13)
C8—C11	1.546 (2)	P1—F3	1.5814 (14)
C11—C16	1.386 (3)	P1—F1	1.5819 (15)
C11—C12	1.396 (3)	P1—F2	1.5842 (13)
C12—C13	1.385 (2)	P1—F5	1.5924 (13)
C12—H12A	0.9500	P1—F6	1.6202 (13)
C7—S1—C8	105.13 (8)	C14—C13—H13A	120.1
C1—N1—C6	125.84 (15)	C12—C13—H13A	120.1
C1—N1—H1A	117.1	C15—C14—C13	119.59 (17)
C6—N1—H1A	117.1	C15—C14—H14A	120.2
C1—N2—C3	122.00 (16)	C13—C14—H14A	120.2
C1—N2—C2	122.76 (17)	C14—C15—C16	120.53 (18)
C3—N2—C2	114.95 (16)	C14—C15—H15A	119.7
C1—N3—C5	122.70 (17)	C16—C15—H15A	119.7
C1—N3—C4	121.96 (18)	C11—C16—C15	120.46 (18)
C5—N3—C4	115.28 (17)	C11—C16—H16A	119.8
N3—C1—N2	120.65 (17)	C15—C16—H16A	119.8
N3—C1—N1	120.34 (17)	C22—C21—C26	117.89 (17)
N2—C1—N1	119.01 (17)	C22—C21—C8	119.67 (15)
N2—C2—H2A	109.5	C26—C21—C8	122.42 (17)
N2—C2—H2B	109.5	C23—C22—C21	121.25 (17)
H2A—C2—H2B	109.5	C23—C22—H22A	119.4
N2—C2—H2C	109.5	C21—C22—H22A	119.4
H2A—C2—H2C	109.5	C22—C23—C24	120.33 (18)
H2B—C2—H2C	109.5	C22—C23—H23A	119.8
N2—C3—H3A	109.5	C24—C23—H23A	119.8
N2—C3—H3B	109.5	C25—C24—C23	119.29 (18)
H3A—C3—H3B	109.5	C25—C24—H24A	120.4
N2—C3—H3C	109.5	C23—C24—H24A	120.4
H3A—C3—H3C	109.5	C24—C25—C26	120.40 (17)
H3B—C3—H3C	109.5	C24—C25—H25A	119.8
N3—C4—H4A	109.5	C26—C25—H25A	119.8
N3—C4—H4B	109.5	C21—C26—C25	120.84 (18)
H4A—C4—H4B	109.5	C21—C26—H26A	119.6
N3—C4—H4C	109.5	C25—C26—H26A	119.6
H4A—C4—H4C	109.5	C36—C31—C32	117.81 (17)
H4B—C4—H4C	109.5	C36—C31—C8	123.97 (16)
N3—C5—H5A	109.5	C32—C31—C8	118.22 (16)
N3—C5—H5B	109.5	C33—C32—C31	121.00 (18)
H5A—C5—H5B	109.5	C33—C32—H32A	119.5
N3—C5—H5C	109.5	C31—C32—H32A	119.5
H5A—C5—H5C	109.5	C32—C33—C34	120.39 (18)
H5B—C5—H5C	109.5	C32—C33—H33A	119.8
N1—C6—C7	112.59 (15)	C34—C33—H33A	119.8
N1—C6—H6A	109.1	C35—C34—C33	119.25 (18)
C7—C6—H6A	109.1	C35—C34—H34A	120.4
N1—C6—H6B	109.1	C33—C34—H34A	120.4
C7—C6—H6B	109.1	C34—C35—C36	120.53 (18)
H6A—C6—H6B	107.8	C34—C35—H35A	119.7
C6—C7—S1	110.58 (12)	C36—C35—H35A	119.7
C6—C7—H7A	109.5	C35—C36—C31	121.02 (18)
S1—C7—H7A	109.5	C35—C36—H36A	119.5
C6—C7—H7B	109.5	C31—C36—H36A	119.5
S1—C7—H7B	109.5	F4—P1—F3	90.03 (8)
H7A—C7—H7B	108.1	F4—P1—F1	91.33 (9)
C21—C8—C31	112.93 (14)	F3—P1—F1	178.58 (9)
C21—C8—C11	111.65 (14)	F4—P1—F2	91.47 (8)
C31—C8—C11	108.14 (14)	F3—P1—F2	89.85 (8)
C21—C8—S1	108.93 (12)	F1—P1—F2	90.54 (9)
C31—C8—S1	112.31 (12)	F4—P1—F5	90.31 (8)
C11—C8—S1	102.41 (11)	F3—P1—F5	89.46 (8)
C16—C11—C12	118.30 (16)	F1—P1—F5	90.11 (9)
C16—C11—C8	123.45 (16)	F2—P1—F5	178.08 (8)
C12—C11—C8	118.19 (16)	F4—P1—F6	179.38 (9)
C13—C12—C11	121.31 (18)	F3—P1—F6	89.43 (8)
C13—C12—H12A	119.3	F1—P1—F6	89.21 (9)
C11—C12—H12A	119.3	F2—P1—F6	88.82 (7)
C14—C13—C12	119.82 (18)	F5—P1—F6	89.39 (7)
C5—N3—C1—N2	−150.95 (18)	C14—C15—C16—C11	−0.4 (3)
C4—N3—C1—N2	32.1 (3)	C31—C8—C21—C22	−174.76 (15)
C5—N3—C1—N1	28.1 (3)	C11—C8—C21—C22	63.1 (2)
C4—N3—C1—N1	−148.85 (18)	S1—C8—C21—C22	−49.25 (19)
C3—N2—C1—N3	−154.99 (18)	C31—C8—C21—C26	6.9 (2)
C2—N2—C1—N3	31.5 (3)	C11—C8—C21—C26	−115.21 (18)
C3—N2—C1—N1	25.9 (3)	S1—C8—C21—C26	132.42 (15)
C2—N2—C1—N1	−147.63 (19)	C26—C21—C22—C23	0.0 (3)
C6—N1—C1—N3	37.8 (3)	C8—C21—C22—C23	−178.44 (16)
C6—N1—C1—N2	−143.12 (19)	C21—C22—C23—C24	0.1 (3)
C1—N1—C6—C7	43.2 (3)	C22—C23—C24—C25	−0.1 (3)
N1—C6—C7—S1	158.36 (13)	C23—C24—C25—C26	0.0 (3)
C8—S1—C7—C6	115.92 (14)	C22—C21—C26—C25	0.0 (3)
C7—S1—C8—C21	−47.42 (14)	C8—C21—C26—C25	178.32 (16)
C7—S1—C8—C31	78.45 (13)	C24—C25—C26—C21	0.1 (3)
C7—S1—C8—C11	−165.77 (12)	C21—C8—C31—C36	103.47 (19)
C21—C8—C11—C16	9.8 (2)	C11—C8—C31—C36	−132.46 (17)
C31—C8—C11—C16	−115.03 (19)	S1—C8—C31—C36	−20.2 (2)
S1—C8—C11—C16	126.21 (16)	C21—C8—C31—C32	−76.83 (19)
C21—C8—C11—C12	−173.28 (15)	C11—C8—C31—C32	47.2 (2)
C31—C8—C11—C12	61.9 (2)	S1—C8—C31—C32	159.51 (14)
S1—C8—C11—C12	−56.87 (18)	C36—C31—C32—C33	0.7 (3)
C16—C11—C12—C13	−0.3 (3)	C8—C31—C32—C33	−179.02 (16)
C8—C11—C12—C13	−177.34 (17)	C31—C32—C33—C34	0.1 (3)
C11—C12—C13—C14	0.4 (3)	C32—C33—C34—C35	−0.8 (3)
C12—C13—C14—C15	−0.5 (3)	C33—C34—C35—C36	0.8 (3)
C13—C14—C15—C16	0.5 (3)	C34—C35—C36—C31	0.0 (3)
C12—C11—C16—C15	0.3 (3)	C32—C31—C36—C35	−0.7 (3)
C8—C11—C16—C15	177.21 (17)	C8—C31—C36—C35	178.97 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···F6i	0.88	2.13	2.949 (2)	155.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯F6i	0.88	2.13	2.949 (2)	155

Symmetry code: (i) .