Mol­ecular structures of 3-[(2,2,3,3-tetra­fluoro­prop­oxy)meth­yl]- and 3-[(2,2,3,3,3-penta­fluoro­prop­oxy)meth­yl]pyridinium saccharinates

The salts 3-[(2,2,3,3-tetra­fluoro­prop­oxy)meth­yl]pyridinium saccharinate, C₉H₁₀F₄NO⁺·C₇H₄NO₃S⁻, (1), and 3-[(2,2,3,3,3-penta­fluoro­prop­oxy)meth­yl]pyridinium saccharinate, C₉H₉F₅NO⁺·C₇H₄NO₃S⁻, (2), i.e. saccharinate (or 1,1-di­oxo-1λ⁶,2-benzo­thia­zol-3-olate) salts of pyridinium with –CH₂OCH₂CF₂CF₂H and –CH₂OCH₂CF₂CF₃ meta substituents, respectively, were investigated crystallographically in order to compare their fluorine-related weak inter­actions in the solid state. Both salts demonstrate a stable synthon formed by the pyridinium cation and the saccharinate anion, in which a seven-membered ring reveals a double hydrogen-bonding pattern. The twist between the pyridinium plane and the saccharinate plane in (2) is 21.26 (8)° and that in (1) is 8.03 (6)°. Both salts also show stacks of alternating cation–anion π-inter­actions. The layer distances, calculated from the centroid of the saccharinate plane to the neighbouring pyridinium planes, above and below, are 3.406 (2) and 3.517 (2) Å in (1), and 3.409 (3) and 3.458 (3) Å in (2).

Computing details

For both structures, data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for i16180; SHELXT2014 (Sheldrick, 2015a) for i16220. For both structures, program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015b). Molecular graphics: SHELXTL (Sheldrick, 2008) and ORTEP-3 (Farrugia, 2012) for i16180; shelXle (Hübschle et al., 2011) and ORTEP-3 (Farrugia, 2012) for i16220. For both structures, software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

3-[(2,2,3,3-Tetrafluoropropoxy)methyl]pyridinium 1,1-dioxo-1λ⁶,2-benzothiazol-3-olate (i16180)

Crystal data

C9H10F4NO^+·C7H4NO3S^−	Z = 2
Mr = 406.35	F(000) = 416
Triclinic, P1	Dx = 1.553 Mg m^−3
a = 7.0975 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.9093 (4) Å	Cell parameters from 6120 reflections
c = 16.9976 (10) Å	θ = 2.4–27.2°
α = 86.160 (2)°	µ = 0.25 mm^−1
β = 83.141 (2)°	T = 100 K
γ = 66.564 (2)°	Prism, colourless
V = 869.00 (8) Å^3	0.30 × 0.26 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer	3373 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.032
Absorption correction: multi-scan (SADABS; Bruker, 1996)	θmax = 27.1°, θmin = 2.4°
Tmin = 0.916, Tmax = 0.971	h = −9→9
28835 measured reflections	k = −10→10
3820 independent reflections	l = −21→21

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	All H-atom parameters refined
wR(F^2) = 0.081	w = 1/[σ^2(Fo^2) + (0.0393P)^2 + 0.4196P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3820 reflections	Δρmax = 0.32 e Å^−3
300 parameters	Δρmin = −0.45 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.35806 (5)	0.49167 (4)	0.29743 (2)	0.01475 (9)
F1	0.29711 (16)	−0.15060 (14)	1.02460 (5)	0.0373 (2)
F2	0.55352 (16)	−0.20619 (15)	0.93201 (6)	0.0429 (3)
F3	0.06885 (18)	−0.21115 (16)	0.91833 (6)	0.0466 (3)
F4	0.3575 (2)	−0.44233 (15)	0.93740 (7)	0.0585 (3)
O1	0.28821 (16)	0.05468 (14)	0.83376 (6)	0.0243 (2)
O2	0.19721 (15)	0.65436 (13)	0.50042 (5)	0.0205 (2)
O3	0.22616 (15)	0.44356 (13)	0.25365 (6)	0.0200 (2)
O4	0.57632 (15)	0.39922 (13)	0.27409 (6)	0.0212 (2)
N1	0.23986 (17)	0.35375 (16)	0.58367 (7)	0.0161 (2)
N2	0.30893 (18)	0.46823 (15)	0.39214 (7)	0.0174 (2)
C1	0.2172 (2)	0.36533 (18)	0.66245 (8)	0.0170 (3)
C2	0.2369 (2)	0.21249 (18)	0.71042 (8)	0.0160 (3)
C3	0.2829 (2)	0.04654 (18)	0.67423 (8)	0.0170 (3)
C4	0.3039 (2)	0.03841 (19)	0.59224 (8)	0.0183 (3)
C5	0.2815 (2)	0.19507 (19)	0.54746 (8)	0.0172 (3)
C6	0.2040 (2)	0.23229 (19)	0.79875 (8)	0.0198 (3)
C7	0.2486 (3)	0.0557 (2)	0.91698 (8)	0.0262 (3)
C8	0.3435 (3)	−0.1417 (2)	0.94458 (9)	0.0299 (3)
C9	0.2768 (3)	−0.2714 (2)	0.90490 (10)	0.0355 (4)
C10	0.2451 (2)	0.63058 (17)	0.42753 (8)	0.0154 (3)
C11	0.22981 (19)	0.78943 (17)	0.37201 (7)	0.0138 (3)
C12	0.1625 (2)	0.97399 (18)	0.38926 (8)	0.0165 (3)
C13	0.1549 (2)	1.09764 (18)	0.32657 (9)	0.0192 (3)
C14	0.2103 (2)	1.03894 (19)	0.24868 (8)	0.0199 (3)
C15	0.2754 (2)	0.85364 (19)	0.23110 (8)	0.0178 (3)
C16	0.28530 (19)	0.73278 (17)	0.29448 (8)	0.0143 (2)
H1	0.223 (3)	0.458 (3)	0.5539 (11)	0.037 (5)*
H1A	0.187 (2)	0.484 (2)	0.6835 (9)	0.011 (3)*
H3	0.296 (2)	−0.058 (2)	0.7048 (9)	0.020 (4)*
H4	0.332 (3)	−0.074 (2)	0.5656 (10)	0.025 (4)*
H5	0.292 (2)	0.205 (2)	0.4923 (10)	0.015 (4)*
H6A	0.269 (2)	0.310 (2)	0.8144 (9)	0.020 (4)*
H6B	0.058 (3)	0.291 (2)	0.8163 (10)	0.021 (4)*
H7A	0.103 (3)	0.103 (2)	0.9332 (10)	0.027 (4)*
H7B	0.311 (3)	0.125 (3)	0.9400 (11)	0.035 (5)*
H9	0.314 (3)	−0.278 (2)	0.8501 (11)	0.030 (5)*
H12	0.116 (2)	1.017 (2)	0.4415 (10)	0.022 (4)*
H13	0.109 (3)	1.228 (2)	0.3360 (10)	0.029 (4)*
H14	0.206 (3)	1.126 (2)	0.2071 (10)	0.028 (4)*
H15	0.313 (2)	0.810 (2)	0.1793 (10)	0.019 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01813 (17)	0.01125 (15)	0.01445 (16)	−0.00577 (12)	−0.00025 (12)	−0.00012 (11)
F1	0.0536 (6)	0.0401 (6)	0.0120 (4)	−0.0128 (5)	−0.0054 (4)	0.0077 (4)
F2	0.0346 (6)	0.0489 (6)	0.0322 (5)	−0.0034 (5)	−0.0080 (4)	0.0112 (5)
F3	0.0507 (7)	0.0542 (7)	0.0373 (6)	−0.0228 (6)	−0.0043 (5)	−0.0040 (5)
F4	0.0927 (10)	0.0309 (6)	0.0469 (7)	−0.0171 (6)	−0.0236 (6)	0.0164 (5)
O1	0.0309 (6)	0.0228 (5)	0.0112 (5)	−0.0030 (4)	−0.0011 (4)	0.0038 (4)
O2	0.0294 (6)	0.0182 (5)	0.0124 (5)	−0.0090 (4)	0.0005 (4)	0.0013 (4)
O3	0.0265 (5)	0.0175 (5)	0.0191 (5)	−0.0116 (4)	−0.0034 (4)	−0.0008 (4)
O4	0.0195 (5)	0.0167 (5)	0.0243 (5)	−0.0045 (4)	0.0020 (4)	−0.0041 (4)
N1	0.0160 (5)	0.0161 (5)	0.0158 (5)	−0.0063 (4)	−0.0023 (4)	0.0034 (4)
N2	0.0223 (6)	0.0139 (5)	0.0152 (6)	−0.0068 (5)	−0.0016 (4)	0.0025 (4)
C1	0.0162 (6)	0.0173 (6)	0.0180 (7)	−0.0068 (5)	−0.0031 (5)	0.0005 (5)
C2	0.0130 (6)	0.0195 (6)	0.0145 (6)	−0.0052 (5)	−0.0025 (5)	0.0017 (5)
C3	0.0168 (6)	0.0154 (6)	0.0170 (6)	−0.0050 (5)	−0.0021 (5)	0.0034 (5)
C4	0.0183 (7)	0.0164 (6)	0.0187 (7)	−0.0055 (5)	−0.0008 (5)	−0.0013 (5)
C5	0.0164 (6)	0.0206 (7)	0.0136 (6)	−0.0063 (5)	−0.0014 (5)	0.0008 (5)
C6	0.0216 (7)	0.0196 (7)	0.0156 (7)	−0.0054 (6)	−0.0022 (5)	0.0009 (5)
C7	0.0323 (9)	0.0290 (8)	0.0123 (7)	−0.0074 (7)	−0.0018 (6)	0.0015 (6)
C8	0.0336 (9)	0.0350 (9)	0.0129 (7)	−0.0057 (7)	−0.0023 (6)	0.0054 (6)
C9	0.0501 (11)	0.0279 (8)	0.0209 (8)	−0.0080 (8)	−0.0050 (7)	0.0060 (6)
C10	0.0144 (6)	0.0151 (6)	0.0167 (6)	−0.0059 (5)	−0.0024 (5)	0.0017 (5)
C11	0.0134 (6)	0.0144 (6)	0.0144 (6)	−0.0063 (5)	−0.0020 (5)	0.0016 (5)
C12	0.0176 (6)	0.0155 (6)	0.0173 (6)	−0.0077 (5)	−0.0003 (5)	−0.0021 (5)
C13	0.0190 (7)	0.0124 (6)	0.0264 (7)	−0.0067 (5)	−0.0019 (5)	0.0008 (5)
C14	0.0229 (7)	0.0179 (7)	0.0205 (7)	−0.0104 (6)	−0.0046 (5)	0.0076 (5)
C15	0.0201 (7)	0.0197 (7)	0.0145 (6)	−0.0093 (5)	−0.0018 (5)	0.0016 (5)
C16	0.0140 (6)	0.0121 (6)	0.0170 (6)	−0.0055 (5)	−0.0012 (5)	0.0000 (5)

Geometric parameters (Å, º)

S1—O3	1.4362 (10)	C4—C5	1.3732 (19)
S1—O4	1.4432 (10)	C4—H4	0.962 (17)
S1—N2	1.6202 (11)	C5—H5	0.932 (16)
S1—C16	1.7652 (13)	C6—H6A	0.970 (16)
F1—C8	1.3644 (16)	C6—H6B	0.969 (17)
F2—C8	1.3642 (19)	C7—C8	1.501 (2)
F3—C9	1.353 (2)	C7—H7A	0.961 (18)
F4—C9	1.3495 (19)	C7—H7B	0.958 (19)
O1—C7	1.4087 (16)	C8—C9	1.512 (2)
O1—C6	1.4106 (17)	C9—H9	0.936 (18)
O2—C10	1.2512 (16)	C10—C11	1.4960 (17)
N1—C1	1.3345 (17)	C11—C16	1.3810 (18)
N1—C5	1.3441 (18)	C11—C12	1.3835 (18)
N1—H1	0.91 (2)	C12—C13	1.3881 (19)
N2—C10	1.3386 (17)	C12—H12	0.945 (17)
C1—C2	1.3807 (18)	C13—C14	1.391 (2)
C1—H1A	0.961 (15)	C13—H13	0.964 (18)
C2—C3	1.3882 (19)	C14—C15	1.3921 (19)
C2—C6	1.5007 (18)	C14—H14	0.948 (18)
C3—C4	1.3869 (19)	C15—C16	1.3807 (18)
C3—H3	0.926 (17)	C15—H15	0.937 (16)
O3—S1—O4	115.30 (6)	C8—C7—H7B	109.1 (11)
O3—S1—N2	111.69 (6)	H7A—C7—H7B	110.4 (15)
O4—S1—N2	110.41 (6)	F2—C8—F1	106.08 (12)
O3—S1—C16	110.29 (6)	F2—C8—C7	110.31 (14)
O4—S1—C16	110.27 (6)	F1—C8—C7	108.74 (12)
N2—S1—C16	97.46 (6)	F2—C8—C9	107.52 (14)
C7—O1—C6	112.79 (11)	F1—C8—C9	109.32 (13)
C1—N1—C5	122.09 (12)	C7—C8—C9	114.53 (13)
C1—N1—H1	118.4 (12)	F4—C9—F3	107.41 (15)
C5—N1—H1	119.5 (12)	F4—C9—C8	110.34 (14)
C10—N2—S1	110.58 (9)	F3—C9—C8	108.16 (14)
N1—C1—C2	120.83 (12)	F4—C9—H9	108.8 (11)
N1—C1—H1A	116.7 (9)	F3—C9—H9	108.5 (11)
C2—C1—H1A	122.4 (9)	C8—C9—H9	113.4 (11)
C1—C2—C3	118.02 (12)	O2—C10—N2	124.80 (12)
C1—C2—C6	119.25 (12)	O2—C10—C11	120.84 (11)
C3—C2—C6	122.71 (12)	N2—C10—C11	114.35 (11)
C4—C3—C2	120.05 (12)	C16—C11—C12	120.28 (12)
C4—C3—H3	119.8 (10)	C16—C11—C10	111.11 (11)
C2—C3—H3	120.1 (10)	C12—C11—C10	128.55 (12)
C5—C4—C3	119.42 (12)	C11—C12—C13	117.87 (12)
C5—C4—H4	118.7 (10)	C11—C12—H12	121.8 (10)
C3—C4—H4	121.8 (10)	C13—C12—H12	120.2 (10)
N1—C5—C4	119.57 (12)	C12—C13—C14	121.29 (12)
N1—C5—H5	114.0 (9)	C12—C13—H13	120.5 (10)
C4—C5—H5	126.4 (9)	C14—C13—H13	118.2 (10)
O1—C6—C2	108.09 (11)	C13—C14—C15	120.93 (12)
O1—C6—H6A	110.9 (9)	C13—C14—H14	119.5 (10)
C2—C6—H6A	110.1 (9)	C15—C14—H14	119.6 (10)
O1—C6—H6B	109.8 (10)	C16—C15—C14	116.75 (13)
C2—C6—H6B	110.5 (10)	C16—C15—H15	120.2 (10)
H6A—C6—H6B	107.5 (13)	C14—C15—H15	123.1 (10)
O1—C7—C8	106.17 (12)	C15—C16—C11	122.85 (12)
O1—C7—H7A	111.3 (10)	C15—C16—S1	130.71 (10)
C8—C7—H7A	108.6 (10)	C11—C16—S1	106.42 (9)
O1—C7—H7B	111.1 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.91 (2)	1.70 (2)	2.6127 (15)	177.9 (10)
C1—H1A···O4^i	0.960 (15)	2.410 (15)	3.0978 (18)	128.3 (12)
C3—H3···O4^ii	0.925 (15)	2.497 (15)	3.3456 (16)	152.6 (12)
C5—H5···N2	0.932 (17)	2.631 (16)	3.3352 (18)	132.8 (12)
C6—H6B···O3^iii	0.97 (2)	2.600 (17)	3.2871 (18)	128.0 (12)
C9—H9···O4^ii	0.936 (19)	2.295 (18)	3.191 (2)	160.0 (13)
C13—H13···O3^iv	0.968 (15)	2.467 (18)	3.1264 (17)	125.1 (14)
C15—H15···F1^v	0.936 (17)	2.638 (17)	3.497 (2)	152.8 (12)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) −x, −y+1, −z+1; (iv) x, y+1, z; (v) x, y+1, z−1.

3-[(2,2,3,3,3-Pentafluoropropoxy)methyl]pyridinium 1,1-dioxo-1λ⁶,2-benzothiazol-3-olate (i16220)

Crystal data

C9H9F5NO^+·C7H4NO3S^−	Dx = 1.647 Mg m^−3
Mr = 424.34	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4	Cell parameters from 9986 reflections
a = 21.6747 (6) Å	θ = 2.7–26.5°
c = 7.2850 (3) Å	µ = 0.27 mm^−1
V = 3422.4 (2) Å^3	T = 100 K
Z = 8	Prism, colourless
F(000) = 1728	0.32 × 0.30 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer	3671 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.045
Absorption correction: multi-scan (SADABS; Bruker, 1996)	θmax = 27.1°, θmin = 1.3°
Tmin = 0.893, Tmax = 0.971	h = −27→27
42157 measured reflections	k = −27→25
3784 independent reflections	l = −9→9

Refinement

Refinement on F^2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F^2 > 2σ(F^2)] = 0.024	w = 1/[σ^2(Fo^2) + (0.0307P)^2 + 2.0967P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.063	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.22 e Å^−3
3784 reflections	Δρmin = −0.25 e Å^−3
305 parameters	Absolute structure: Flack x determined using 1659 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
0 restraints	Absolute structure parameter: 0.00 (2)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.22877 (2)	0.37464 (2)	0.34576 (7)	0.01336 (12)
F1	0.44207 (7)	0.53864 (7)	0.7307 (3)	0.0350 (4)
F2	0.37236 (8)	0.51192 (8)	0.5285 (2)	0.0356 (4)
F3	0.30619 (7)	0.45483 (7)	0.7899 (3)	0.0366 (4)
F4	0.40121 (8)	0.42684 (7)	0.7968 (3)	0.0400 (4)
F6	0.36623 (9)	0.48909 (8)	1.0015 (2)	0.0394 (4)
O1	0.28427 (7)	0.57889 (7)	0.7130 (2)	0.0188 (3)
O2	0.07648 (7)	0.43765 (7)	0.4578 (2)	0.0183 (3)
O3	0.26829 (7)	0.35527 (8)	0.4953 (2)	0.0182 (3)
O4	0.25989 (7)	0.39279 (8)	0.1799 (2)	0.0213 (4)
N1	0.10858 (8)	0.54978 (9)	0.5636 (3)	0.0150 (4)
N2	0.18044 (9)	0.42747 (8)	0.4134 (3)	0.0151 (4)
C1	0.06506 (10)	0.59377 (10)	0.5597 (3)	0.0159 (4)
C2	0.07973 (10)	0.65316 (11)	0.6117 (3)	0.0160 (4)
C3	0.13946 (10)	0.66627 (10)	0.6681 (3)	0.0151 (4)
C4	0.18392 (10)	0.61986 (10)	0.6727 (3)	0.0135 (4)
C5	0.16693 (10)	0.56132 (10)	0.6171 (3)	0.0140 (4)
C6	0.24893 (10)	0.63352 (10)	0.7320 (3)	0.0147 (4)
C7	0.34778 (10)	0.58895 (11)	0.7457 (4)	0.0202 (5)
C8	0.38100 (10)	0.52927 (11)	0.7043 (4)	0.0212 (5)
C9	0.36311 (11)	0.47400 (11)	0.8250 (4)	0.0241 (5)
C10	0.12257 (10)	0.40642 (10)	0.4104 (3)	0.0138 (4)
C11	0.11611 (10)	0.34075 (9)	0.3468 (3)	0.0133 (4)
C12	0.06331 (10)	0.30515 (10)	0.3293 (3)	0.0163 (4)
C13	0.06977 (11)	0.24424 (11)	0.2698 (3)	0.0191 (5)
C14	0.12767 (12)	0.22022 (11)	0.2278 (3)	0.0195 (5)
C15	0.18080 (11)	0.25613 (11)	0.2423 (3)	0.0171 (5)
C16	0.17344 (10)	0.31628 (10)	0.3031 (3)	0.0136 (4)
H1	0.0972 (14)	0.5101 (15)	0.528 (4)	0.032 (8)*
H1A	0.0258 (12)	0.5813 (12)	0.523 (4)	0.016 (6)*
H2	0.0506 (13)	0.6828 (14)	0.609 (4)	0.024 (7)*
H3	0.1511 (11)	0.7066 (12)	0.706 (4)	0.010 (6)*
H5	0.1927 (13)	0.5290 (13)	0.605 (4)	0.017 (7)*
H6A	0.2654 (12)	0.6643 (13)	0.656 (4)	0.017 (6)*
H6B	0.2480 (11)	0.6501 (11)	0.862 (4)	0.012 (6)*
H7A	0.3546 (13)	0.5995 (13)	0.869 (4)	0.022 (7)*
H7B	0.3630 (13)	0.6202 (14)	0.671 (4)	0.026 (7)*
H12	0.0217 (13)	0.3233 (12)	0.353 (4)	0.021 (7)*
H13	0.0329 (14)	0.2200 (13)	0.253 (4)	0.022 (7)*
H14	0.1313 (14)	0.1785 (14)	0.182 (5)	0.030 (8)*
H15	0.2188 (13)	0.2374 (13)	0.215 (4)	0.024 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0111 (2)	0.0141 (2)	0.0149 (2)	0.00109 (19)	0.00029 (19)	0.0012 (2)
F1	0.0132 (7)	0.0307 (8)	0.0612 (11)	0.0018 (6)	0.0000 (7)	0.0052 (8)
F2	0.0402 (9)	0.0430 (10)	0.0237 (8)	0.0119 (7)	0.0039 (7)	−0.0036 (7)
F3	0.0255 (8)	0.0233 (8)	0.0610 (12)	−0.0076 (6)	−0.0046 (8)	0.0048 (8)
F4	0.0360 (9)	0.0185 (7)	0.0656 (13)	0.0095 (6)	−0.0050 (8)	−0.0009 (8)
F6	0.0559 (11)	0.0351 (9)	0.0272 (9)	0.0025 (8)	−0.0051 (8)	0.0069 (7)
O1	0.0128 (8)	0.0139 (7)	0.0298 (9)	0.0001 (6)	−0.0039 (7)	−0.0021 (7)
O2	0.0126 (7)	0.0136 (7)	0.0286 (9)	0.0023 (6)	−0.0015 (7)	−0.0044 (7)
O3	0.0138 (7)	0.0227 (8)	0.0181 (9)	0.0035 (6)	−0.0023 (6)	0.0001 (7)
O4	0.0178 (8)	0.0271 (8)	0.0189 (8)	−0.0014 (7)	0.0036 (7)	0.0046 (7)
N1	0.0152 (9)	0.0131 (9)	0.0168 (9)	−0.0021 (7)	0.0006 (7)	−0.0011 (7)
N2	0.0134 (8)	0.0116 (8)	0.0204 (9)	0.0023 (7)	−0.0010 (7)	−0.0001 (7)
C1	0.0126 (10)	0.0176 (11)	0.0174 (11)	0.0002 (8)	0.0008 (8)	0.0008 (9)
C2	0.0149 (10)	0.0155 (10)	0.0175 (10)	0.0037 (9)	0.0012 (8)	0.0004 (8)
C3	0.0187 (10)	0.0129 (10)	0.0137 (10)	−0.0006 (8)	0.0015 (9)	−0.0010 (8)
C4	0.0143 (10)	0.0155 (10)	0.0107 (10)	−0.0013 (8)	0.0007 (8)	0.0005 (8)
C5	0.0138 (10)	0.0138 (10)	0.0144 (10)	0.0011 (8)	0.0002 (8)	0.0000 (8)
C6	0.0146 (10)	0.0133 (10)	0.0162 (10)	0.0006 (8)	−0.0009 (8)	−0.0004 (8)
C7	0.0139 (11)	0.0155 (11)	0.0313 (14)	−0.0016 (8)	−0.0048 (10)	0.0020 (10)
C8	0.0155 (11)	0.0222 (12)	0.0260 (12)	0.0006 (9)	−0.0011 (9)	−0.0004 (10)
C9	0.0235 (12)	0.0158 (11)	0.0329 (14)	0.0015 (9)	−0.0053 (11)	0.0006 (10)
C10	0.0148 (10)	0.0118 (10)	0.0147 (10)	0.0010 (8)	−0.0011 (8)	0.0002 (8)
C11	0.0164 (10)	0.0124 (9)	0.0109 (9)	0.0005 (8)	−0.0001 (8)	0.0005 (8)
C12	0.0166 (10)	0.0184 (10)	0.0139 (10)	−0.0006 (8)	−0.0001 (8)	−0.0005 (9)
C13	0.0234 (12)	0.0184 (11)	0.0154 (11)	−0.0062 (9)	−0.0007 (9)	−0.0012 (9)
C14	0.0295 (13)	0.0125 (10)	0.0166 (11)	−0.0008 (9)	−0.0001 (9)	−0.0006 (8)
C15	0.0205 (11)	0.0163 (10)	0.0146 (11)	0.0058 (9)	0.0014 (9)	−0.0010 (8)
C16	0.0141 (10)	0.0141 (10)	0.0126 (10)	−0.0004 (7)	−0.0003 (8)	0.0011 (8)

Geometric parameters (Å, º)

S1—O4	1.4387 (17)	C3—H3	0.95 (3)
S1—O3	1.4480 (17)	C4—C5	1.382 (3)
S1—N2	1.6283 (19)	C4—C6	1.503 (3)
S1—C16	1.771 (2)	C5—H5	0.90 (3)
F1—C8	1.353 (3)	C6—H6A	0.94 (3)
F2—C8	1.348 (3)	C6—H6B	1.02 (3)
F3—C9	1.327 (3)	C7—C8	1.511 (3)
F4—C9	1.330 (3)	C7—H7A	0.94 (3)
F6—C9	1.329 (3)	C7—H7B	0.93 (3)
O1—C7	1.414 (3)	C8—C9	1.535 (3)
O1—C6	1.417 (3)	C10—C11	1.504 (3)
O2—C10	1.255 (3)	C11—C12	1.386 (3)
N1—C1	1.342 (3)	C11—C16	1.388 (3)
N1—C5	1.347 (3)	C12—C13	1.396 (3)
N1—H1	0.93 (3)	C12—H12	1.00 (3)
N2—C10	1.335 (3)	C13—C14	1.393 (4)
C1—C2	1.379 (3)	C13—H13	0.96 (3)
C1—H1A	0.93 (3)	C14—C15	1.394 (3)
C2—C3	1.388 (3)	C14—H14	0.97 (3)
C2—H2	0.90 (3)	C15—C16	1.386 (3)
C3—C4	1.393 (3)	C15—H15	0.94 (3)
O4—S1—O3	115.71 (10)	C8—C7—H7B	109.8 (18)
O4—S1—N2	111.31 (10)	H7A—C7—H7B	109 (3)
O3—S1—N2	110.92 (10)	F2—C8—F1	108.2 (2)
O4—S1—C16	111.44 (10)	F2—C8—C7	111.2 (2)
O3—S1—C16	108.99 (10)	F1—C8—C7	108.02 (19)
N2—S1—C16	96.88 (10)	F2—C8—C9	106.9 (2)
C7—O1—C6	112.40 (17)	F1—C8—C9	106.4 (2)
C1—N1—C5	122.3 (2)	C7—C8—C9	115.7 (2)
C1—N1—H1	117.6 (19)	F3—C9—F6	108.1 (2)
C5—N1—H1	120.1 (19)	F3—C9—F4	107.9 (2)
C10—N2—S1	111.06 (15)	F6—C9—F4	107.9 (2)
N1—C1—C2	119.7 (2)	F3—C9—C8	111.6 (2)
N1—C1—H1A	116.2 (17)	F6—C9—C8	110.4 (2)
C2—C1—H1A	124.1 (17)	F4—C9—C8	110.8 (2)
C1—C2—C3	119.2 (2)	O2—C10—N2	124.0 (2)
C1—C2—H2	120.0 (19)	O2—C10—C11	121.4 (2)
C3—C2—H2	120.8 (19)	N2—C10—C11	114.58 (18)
C2—C3—C4	120.3 (2)	C12—C11—C16	120.36 (19)
C2—C3—H3	121.5 (15)	C12—C11—C10	129.21 (19)
C4—C3—H3	118.2 (15)	C16—C11—C10	110.43 (18)
C5—C4—C3	118.1 (2)	C11—C12—C13	118.2 (2)
C5—C4—C6	121.0 (2)	C11—C12—H12	120.7 (16)
C3—C4—C6	120.87 (19)	C13—C12—H12	121.0 (16)
N1—C5—C4	120.4 (2)	C14—C13—C12	120.8 (2)
N1—C5—H5	114.2 (18)	C14—C13—H13	121.0 (17)
C4—C5—H5	125.3 (18)	C12—C13—H13	118.1 (17)
O1—C6—C4	108.30 (18)	C13—C14—C15	121.3 (2)
O1—C6—H6A	109.3 (16)	C13—C14—H14	119.9 (18)
C4—C6—H6A	109.1 (16)	C15—C14—H14	118.8 (18)
O1—C6—H6B	113.4 (14)	C16—C15—C14	117.0 (2)
C4—C6—H6B	108.7 (14)	C16—C15—H15	125.0 (17)
H6A—C6—H6B	108 (2)	C14—C15—H15	117.9 (17)
O1—C7—C8	107.36 (18)	C15—C16—C11	122.4 (2)
O1—C7—H7A	110.6 (18)	C15—C16—S1	130.56 (17)
C8—C7—H7A	108.9 (18)	C11—C16—S1	107.05 (15)
O1—C7—H7B	111.2 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.93 (3)	1.71 (3)	2.643 (2)	179 (3)
C1—H1A···O2^i	0.93 (3)	2.30 (3)	3.229 (3)	172 (2)
C3—H3···O3^ii	0.95 (3)	2.56 (3)	3.304 (3)	136 (2)
C5—H5···N2	0.90 (3)	2.62 (3)	3.272 (3)	130 (2)
C6—H6A···O3^iii	0.94 (3)	2.67 (3)	3.547 (3)	156 (2)
C7—H7B···O3^iii	0.93 (3)	2.71 (3)	3.561 (3)	153 (2)
C14—H14···F4^iv	0.97 (3)	2.53 (3)	3.287 (3)	135 (3)
C14—H14···O3^iv	0.97 (3)	2.67 (3)	3.261 (3)	120 (2)
C15—H15···O3^iv	0.94 (3)	2.58 (3)	3.207 (3)	124 (2)

Symmetry codes: (i) −x, −y+1, z; (ii) −y+1/2, x+1/2, −z+3/2; (iii) y, −x+1, −z+1; (iv) −x+1/2, −y+1/2, z−1/2.