Multifunctional aryl­sulfonamide derivatives with 5-HT₆/5-HT₇ receptor antagonistic activity: a structural study

Nowadays, a search for antagonists co-acting on serotonin receptor subtypes 6 and 7 (5-HT₆R and 5-HT₇R, respectively) is of great inter­est due to the increasing number of patients suffering from dementia and related behavioural and psychological symptoms. The X-ray crystal structures of four promising multifunctional ligands in the hydro­chloride forms were determined, namely 4-(6-fluoro-1,2-benzoxazol-3-yl)-1-[3-(3-methyl­benzene­sulfonamido)­prop­yl]pi­peridin-1-ium chloride, C₂₂H₂₇FN₃O₃S⁺·Cl⁻, (I), 4-(6-fluoro-1,2-benzoxazol-3-yl)-1-[4-(5-fluoro-3-methyl­benzo[b]thio­phene-2-sulfonamido)­but­yl]piperidin-1-ium chloride, C₂₅H₂₈F₂N₃O₃S₂⁺·Cl⁻, (II), 4-(6-fluoro-1,2-benzoxazol-3-yl)-1-[4-(6-fluoro­benzo[b]thio­phene-2-sulfonamido)­but­yl]piperidin-1-ium chloride, C₂₄H₂₆ClFN₃O₃S₂⁺·Cl⁻, (III), and 4-(6-fluoro-1,2-benzoxazol-3-yl)-1-[3-(3-chloro-4-fluoro­benzene­sulfonamido)­prop­yl]piperidin-1-ium chloride, C₂₁H₂₂ClF₂N₃O₃S₂⁺·Cl⁻, (IV). Two pharmacologically important functional groups, i.e. aryl­sulfonamide and piperidinyl–fluoro­benzisoxazole, are linked by three- and four-membered aliphatic chains. These compounds crystallize as hydro­chloride salts in monoclinic space groups, i.e. C2/c for (I), P2₁/c for (II) and (III), and P2₁/n for (IV). In the asymmetric unit, a charge-assisted hydrogen bond is observed between the cation located at the piperidine N atom and the chloride anion. The protonated piperidine N atom is critical to the pharmacological activity for the compounds, allowing for a strong inter­action with mono­amine­rgic receptors in the central nervous system. The sulfonyl group plays the role of a hydrogen-bond acceptor in the pharmacophore model and is involved in several C—H...O inter­actions. Two aromatic fragments of the presented structures are involved in C—H...π contacts, which were studied by Hirshfeld structure analysis. The distances between the mentioned functional groups are in agreement with pharmacophore models given in the literature. The studied inter­actions observed in the crystal structure indicate the main forces responsible for ligand–receptor recognition and binding.

Computing details

For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).

4-(6-Fluoro-1,2-benzoxazol-3-yl)-1-[3-(3-methylbenzenesulfonamido)propyl]piperidin-1-ium chloride (I)

Crystal data

C22H27FN3O3S^+·Cl^−	F(000) = 1968
Mr = 467.97	Dx = 1.351 Mg m^−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 6017 reflections
a = 21.1233 (4) Å	θ = 4.2–70.3°
b = 6.4503 (2) Å	µ = 2.63 mm^−1
c = 33.9243 (9) Å	T = 116 K
β = 95.453 (2)°	Plate, white
V = 4601.3 (2) Å^3	0.2 × 0.2 × 0.02 mm
Z = 8

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	4449 independent reflections
Mirror monochromator	3374 reflections with I > 2σ(I)
Detector resolution: 10.3756 pixels mm^-1	Rint = 0.077
ω scans	θmax = 71.3°, θmin = 4.2°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −25→25
Tmin = 0.631, Tmax = 1	k = −7→7
30959 measured reflections	l = −41→41

Refinement

Refinement on F^2	14 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0445P)^2 + 5.0472P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
4449 reflections	Δρmax = 0.27 e Å^−3
360 parameters	Δρmin = −0.39 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	Occ. (<1)
S21	0.03439 (2)	−0.04760 (9)	0.18821 (2)	0.02593 (14)
Cl1	0.27607 (2)	0.33886 (9)	0.32176 (2)	0.03225 (15)
O21B	0.03759 (7)	−0.2543 (3)	0.20382 (5)	0.0336 (4)
O21A	−0.01604 (7)	0.0877 (3)	0.19743 (5)	0.0339 (4)
N13	0.14419 (8)	0.5204 (3)	0.29581 (5)	0.0229 (4)
N20	0.10115 (9)	0.0613 (3)	0.20281 (6)	0.0271 (4)
C17	0.15028 (10)	0.3900 (4)	0.22626 (6)	0.0280 (5)
H17A	0.1895	0.3108	0.2344	0.034*
H17B	0.1627	0.5295	0.2176	0.034*
C18	0.11220 (11)	0.2794 (4)	0.19223 (6)	0.0294 (5)
H18A	0.0709	0.3503	0.1861	0.035*
H18B	0.1357	0.2847	0.1683	0.035*
C10	0.15574 (10)	0.8370 (4)	0.35865 (7)	0.0320 (5)
H10	0.1154	0.916	0.3521	0.038*
C12	0.10547 (10)	0.5048 (4)	0.33071 (6)	0.0278 (5)
H12A	0.0986	0.3568	0.3368	0.033*
H12B	0.0634	0.5695	0.3239	0.033*
C16	0.11054 (10)	0.4097 (3)	0.26110 (6)	0.0259 (5)
H16A	0.0709	0.4854	0.2524	0.031*
H16B	0.0986	0.2693	0.2695	0.031*
C15	0.19407 (11)	0.8441 (4)	0.32259 (7)	0.0329 (5)
H15A	0.2032	0.9902	0.3162	0.04*
H15B	0.2352	0.7722	0.3289	0.04*
C22	0.02829 (10)	−0.0709 (4)	0.13608 (7)	0.0305 (5)
C14	0.15817 (11)	0.7423 (3)	0.28709 (7)	0.0298 (5)
H14A	0.1178	0.8175	0.2801	0.036*
H14B	0.1838	0.7497	0.2642	0.036*
C11	0.13823 (11)	0.6107 (4)	0.36694 (7)	0.0327 (5)
H11A	0.1774	0.5332	0.376	0.039*
H11B	0.1098	0.6076	0.3885	0.039*
C23	−0.00397 (12)	0.0804 (5)	0.11292 (7)	0.0437 (7)
H23	−0.0207	0.1975	0.1253	0.052*
C27	0.05460 (16)	−0.2407 (5)	0.11926 (9)	0.0530 (8)
H27	0.0781	−0.3409	0.1351	0.064*
C25	0.01186 (19)	−0.1125 (6)	0.05565 (9)	0.0712 (11)
H25	0.0048	−0.1317	0.0278	0.085*
N1	0.1703 (3)	1.1099 (8)	0.40732 (14)	0.0407 (10)	0.834 (4)
O2	0.2120 (3)	1.1647 (8)	0.44130 (15)	0.0543 (12)	0.834 (4)
C3	0.25764 (19)	1.0166 (7)	0.44597 (13)	0.0539 (12)	0.834 (4)
C4	0.3072 (2)	1.0094 (10)	0.47622 (17)	0.0788 (19)	0.834 (4)
H4	0.3129	1.1101	0.4967	0.095*	0.834 (4)
C5	0.3466 (2)	0.8448 (10)	0.47363 (18)	0.0875 (19)	0.834 (4)
F5	0.39628 (18)	0.8243 (7)	0.50254 (13)	0.137 (2)	0.834 (4)
C6	0.3409 (2)	0.6939 (8)	0.44443 (15)	0.0779 (18)	0.834 (4)
H6	0.3712	0.5846	0.4447	0.094*	0.834 (4)
C7	0.29119 (19)	0.7031 (7)	0.41500 (14)	0.0511 (11)	0.834 (4)
H7	0.286	0.6009	0.3948	0.061*	0.834 (4)
C8	0.24853 (18)	0.8696 (7)	0.41612 (12)	0.0417 (10)	0.834 (4)
C9	0.1917 (2)	0.9393 (8)	0.39323 (11)	0.0333 (10)	0.834 (4)
N1A	0.1618 (15)	1.068 (5)	0.4161 (9)	0.0407 (10)	0.166 (4)
O2A	0.1995 (13)	1.110 (4)	0.4537 (7)	0.043 (5)	0.166 (4)
C3A	0.2413 (11)	0.952 (4)	0.4599 (7)	0.0539 (12)	0.166 (4)
C4A	0.2828 (10)	0.935 (4)	0.4920 (7)	0.053 (6)	0.166 (4)
H4A	0.287	1.0355	0.5125	0.063*	0.166 (4)
C5A	0.3184 (10)	0.758 (4)	0.4923 (6)	0.053 (6)	0.166 (4)
F5A	0.3612 (6)	0.722 (2)	0.5241 (4)	0.075 (4)	0.166 (4)
C6A	0.3166 (11)	0.613 (5)	0.4634 (8)	0.0779 (18)	0.166 (4)
H6A	0.3445	0.4969	0.4657	0.094*	0.166 (4)
C7A	0.2723 (10)	0.637 (4)	0.4301 (6)	0.042 (5)	0.166 (4)
H7A	0.268	0.535	0.4098	0.05*	0.166 (4)
C8A	0.2349 (11)	0.816 (4)	0.4276 (7)	0.0417 (10)	0.166 (4)
C9A	0.1845 (16)	0.898 (5)	0.4012 (6)	0.0333 (10)	0.166 (4)
C26	0.0456 (2)	−0.2611 (6)	0.07806 (10)	0.0789 (12)
C28	−0.0451 (2)	0.2396 (8)	0.04751 (11)	0.0687 (13)	0.834 (4)
H28A	−0.066	0.3332	0.065	0.103*	0.834 (4)
H28B	−0.0769	0.1809	0.0277	0.103*	0.834 (4)
H28C	−0.0134	0.3168	0.0341	0.103*	0.834 (4)
C24	−0.01214 (14)	0.0634 (6)	0.07216 (8)	0.0572 (8)
C28A	0.0987 (10)	−0.451 (4)	0.0673 (5)	0.0687 (13)	0.166 (4)
H28D	0.0917	−0.5757	0.0829	0.103*	0.166 (4)
H28E	0.1423	−0.4014	0.074	0.103*	0.166 (4)
H28F	0.0925	−0.4848	0.0391	0.103*	0.166 (4)
H13	0.1819 (12)	0.458 (4)	0.3026 (7)	0.033 (7)*
H20	0.1322 (12)	−0.021 (4)	0.1983 (7)	0.033 (7)*
H24	−0.045 (4)	0.139 (12)	0.0572 (10)	0.049*	0.166 (4)
H26	0.0529 (16)	−0.391 (2)	0.0661 (6)	0.049*	0.834 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S21	0.0185 (2)	0.0304 (3)	0.0289 (3)	0.0025 (2)	0.0024 (2)	−0.0006 (2)
Cl1	0.0189 (2)	0.0275 (3)	0.0506 (4)	−0.0002 (2)	0.0047 (2)	−0.0035 (2)
O21B	0.0285 (8)	0.0297 (9)	0.0423 (9)	−0.0012 (7)	0.0008 (7)	0.0041 (7)
O21A	0.0235 (8)	0.0447 (10)	0.0342 (9)	0.0107 (7)	0.0052 (7)	0.0003 (8)
N13	0.0170 (8)	0.0222 (9)	0.0296 (10)	−0.0014 (7)	0.0023 (7)	−0.0008 (8)
N20	0.0203 (9)	0.0280 (10)	0.0323 (10)	0.0033 (8)	−0.0005 (8)	−0.0030 (8)
C17	0.0261 (11)	0.0284 (12)	0.0299 (12)	−0.0050 (9)	0.0049 (9)	0.0006 (9)
C18	0.0307 (12)	0.0302 (13)	0.0276 (11)	0.0003 (10)	0.0040 (9)	0.0006 (10)
C10	0.0221 (11)	0.0303 (12)	0.0425 (14)	0.0038 (9)	−0.0023 (10)	−0.0106 (11)
C12	0.0233 (11)	0.0305 (12)	0.0304 (12)	−0.0019 (9)	0.0070 (9)	−0.0001 (10)
C16	0.0204 (10)	0.0290 (12)	0.0282 (11)	−0.0045 (9)	0.0012 (9)	−0.0018 (9)
C15	0.0258 (11)	0.0254 (12)	0.0475 (15)	−0.0044 (9)	0.0028 (10)	−0.0049 (11)
C22	0.0235 (11)	0.0418 (14)	0.0263 (11)	−0.0068 (10)	0.0040 (9)	−0.0045 (10)
C14	0.0280 (12)	0.0226 (11)	0.0394 (13)	−0.0041 (9)	0.0063 (10)	0.0014 (10)
C11	0.0283 (12)	0.0371 (14)	0.0325 (12)	−0.0006 (10)	0.0030 (10)	−0.0044 (10)
C23	0.0307 (13)	0.070 (2)	0.0314 (13)	0.0079 (13)	0.0068 (10)	0.0041 (13)
C27	0.077 (2)	0.0389 (16)	0.0454 (16)	−0.0016 (15)	0.0174 (15)	−0.0074 (13)
C25	0.089 (3)	0.092 (3)	0.0327 (16)	−0.035 (2)	0.0056 (17)	−0.0113 (18)
N1	0.034 (2)	0.038 (3)	0.049 (3)	0.0028 (16)	−0.0058 (16)	−0.0183 (18)
O2	0.043 (2)	0.056 (3)	0.061 (3)	0.0109 (19)	−0.012 (2)	−0.036 (2)
C3	0.037 (2)	0.059 (3)	0.063 (3)	0.0124 (18)	−0.0110 (18)	−0.029 (2)
C4	0.045 (3)	0.102 (5)	0.083 (4)	0.020 (3)	−0.027 (2)	−0.059 (4)
C5	0.049 (3)	0.114 (5)	0.090 (4)	0.031 (3)	−0.043 (3)	−0.051 (4)
F5	0.087 (3)	0.169 (4)	0.137 (3)	0.064 (3)	−0.082 (2)	−0.092 (3)
C6	0.050 (3)	0.090 (4)	0.087 (4)	0.034 (2)	−0.031 (2)	−0.042 (3)
C7	0.032 (2)	0.059 (3)	0.058 (3)	0.0160 (19)	−0.0135 (19)	−0.026 (2)
C8	0.029 (2)	0.046 (3)	0.048 (3)	0.0052 (15)	−0.0060 (15)	−0.0201 (18)
C9	0.0253 (18)	0.032 (3)	0.042 (2)	−0.0001 (15)	0.0004 (16)	−0.0102 (18)
N1A	0.034 (2)	0.038 (3)	0.049 (3)	0.0028 (16)	−0.0058 (16)	−0.0183 (18)
O2A	0.034 (10)	0.051 (13)	0.042 (11)	0.010 (8)	−0.002 (7)	−0.016 (8)
C3A	0.037 (2)	0.059 (3)	0.063 (3)	0.0124 (18)	−0.0110 (18)	−0.029 (2)
C4A	0.029 (11)	0.074 (16)	0.052 (13)	0.017 (10)	−0.010 (9)	−0.034 (11)
C5A	0.035 (10)	0.080 (16)	0.040 (11)	0.007 (10)	−0.014 (8)	−0.024 (10)
F5A	0.039 (7)	0.105 (11)	0.077 (9)	0.020 (7)	−0.023 (6)	−0.019 (8)
C6A	0.050 (3)	0.090 (4)	0.087 (4)	0.034 (2)	−0.031 (2)	−0.042 (3)
C7A	0.036 (11)	0.055 (13)	0.035 (11)	−0.002 (9)	0.003 (8)	−0.020 (9)
C8A	0.029 (2)	0.046 (3)	0.048 (3)	0.0052 (15)	−0.0060 (15)	−0.0201 (18)
C9A	0.0253 (18)	0.032 (3)	0.042 (2)	−0.0001 (15)	0.0004 (16)	−0.0102 (18)
C26	0.139 (4)	0.049 (2)	0.054 (2)	−0.019 (2)	0.036 (2)	−0.0243 (18)
C28	0.063 (2)	0.109 (4)	0.0340 (18)	0.012 (2)	0.0041 (17)	0.021 (2)
C24	0.0421 (16)	0.096 (3)	0.0337 (15)	−0.0044 (17)	0.0064 (12)	0.0046 (17)
C28A	0.063 (2)	0.109 (4)	0.0340 (18)	0.012 (2)	0.0041 (17)	0.021 (2)

Geometric parameters (Å, º)

S21—O21B	1.4339 (17)	C25—H25	0.95
S21—O21A	1.4344 (16)	N1—C9	1.299 (8)
S21—N20	1.6110 (19)	N1—O2	1.427 (8)
S21—C22	1.767 (2)	O2—C3	1.356 (7)
N13—C14	1.496 (3)	C3—C8	1.387 (6)
N13—C16	1.497 (3)	C3—C4	1.396 (6)
N13—C12	1.505 (3)	C4—C5	1.356 (7)
N13—H13	0.90 (3)	C4—H4	0.95
N20—C18	1.476 (3)	C5—F5	1.373 (5)
N20—H20	0.87 (3)	C5—C6	1.386 (6)
C17—C16	1.519 (3)	C6—C7	1.380 (6)
C17—C18	1.521 (3)	C6—H6	0.95
C17—H17A	0.99	C7—C8	1.405 (6)
C17—H17B	0.99	C7—H7	0.95
C18—H18A	0.99	C8—C9	1.438 (7)
C18—H18B	0.99	N1A—C9A	1.31 (5)
C10—C9	1.490 (5)	N1A—O2A	1.46 (4)
C10—C15	1.531 (3)	O2A—C3A	1.35 (4)
C10—C11	1.538 (3)	C3A—C4A	1.34 (3)
C10—C9A	1.562 (18)	C3A—C8A	1.40 (3)
C10—H10	1	C4A—C5A	1.37 (3)
C12—C11	1.515 (3)	C4A—H4A	0.95
C12—H12A	0.99	C5A—C6A	1.35 (3)
C12—H12B	0.99	C5A—F5A	1.36 (2)
C16—H16A	0.99	C6A—C7A	1.41 (3)
C16—H16B	0.99	C6A—H6A	0.95
C15—C14	1.511 (3)	C7A—C8A	1.39 (3)
C15—H15A	0.99	C7A—H7A	0.95
C15—H15B	0.99	C8A—C9A	1.43 (4)
C22—C27	1.377 (4)	C26—C28A	1.72 (2)
C22—C23	1.390 (4)	C26—H26	0.949 (9)
C14—H14A	0.99	C28—C24	1.538 (5)
C14—H14B	0.99	C28—H28A	0.98
C11—H11A	0.99	C28—H28B	0.98
C11—H11B	0.99	C28—H28C	0.98
C23—C24	1.381 (4)	C28—H24	0.73 (9)
C23—H23	0.95	C24—H24	0.957 (10)
C27—C26	1.399 (4)	C28A—H28D	0.98
C27—H27	0.95	C28A—H28E	0.98
C25—C26	1.379 (5)	C28A—H28F	0.98
C25—C24	1.383 (5)	C28A—H26	1.04 (3)
O21B—S21—O21A	119.67 (10)	C3—O2—N1	107.3 (5)
O21B—S21—N20	106.43 (10)	O2—C3—C8	110.4 (4)
O21A—S21—N20	108.31 (10)	O2—C3—C4	125.8 (4)
O21B—S21—C22	106.68 (11)	C8—C3—C4	123.8 (4)
O21A—S21—C22	106.56 (11)	C5—C4—C3	113.6 (4)
N20—S21—C22	108.86 (10)	C5—C4—H4	123.2
C14—N13—C16	112.87 (17)	C3—C4—H4	123.2
C14—N13—C12	110.61 (17)	C4—C5—F5	117.5 (4)
C16—N13—C12	109.50 (16)	C4—C5—C6	125.8 (4)
C14—N13—H13	107.0 (16)	F5—C5—C6	116.8 (4)
C16—N13—H13	109.2 (16)	C7—C6—C5	119.6 (4)
C12—N13—H13	107.5 (16)	C7—C6—H6	120.2
C18—N20—S21	119.67 (15)	C5—C6—H6	120.2
C18—N20—H20	113.6 (17)	C6—C7—C8	117.4 (4)
S21—N20—H20	109.5 (17)	C6—C7—H7	121.3
C16—C17—C18	109.80 (18)	C8—C7—H7	121.3
C16—C17—H17A	109.7	C3—C8—C7	119.8 (4)
C18—C17—H17A	109.7	C3—C8—C9	103.4 (4)
C16—C17—H17B	109.7	C7—C8—C9	136.8 (4)
C18—C17—H17B	109.7	N1—C9—C8	111.6 (4)
H17A—C17—H17B	108.2	N1—C9—C10	119.7 (5)
N20—C18—C17	110.30 (18)	C8—C9—C10	128.6 (4)
N20—C18—H18A	109.6	C9A—N1A—O2A	108 (3)
C17—C18—H18A	109.6	C3A—O2A—N1A	107 (2)
N20—C18—H18B	109.6	C4A—C3A—O2A	124 (2)
C17—C18—H18B	109.6	C4A—C3A—C8A	126 (2)
H18A—C18—H18B	108.1	O2A—C3A—C8A	110 (2)
C9—C10—C15	110.3 (2)	C3A—C4A—C5A	113 (2)
C9—C10—C11	112.9 (2)	C3A—C4A—H4A	123.4
C15—C10—C11	109.24 (19)	C5A—C4A—H4A	123.4
C15—C10—C9A	122.8 (11)	C6A—C5A—F5A	115 (2)
C11—C10—C9A	98.6 (11)	C6A—C5A—C4A	126.6 (19)
C9—C10—H10	108.1	F5A—C5A—C4A	118.2 (17)
C15—C10—H10	108.1	C5A—C6A—C7A	118 (2)
C11—C10—H10	108.1	C5A—C6A—H6A	120.9
N13—C12—C11	111.56 (18)	C7A—C6A—H6A	120.9
N13—C12—H12A	109.3	C8A—C7A—C6A	118 (2)
C11—C12—H12A	109.3	C8A—C7A—H7A	120.9
N13—C12—H12B	109.3	C6A—C7A—H7A	120.9
C11—C12—H12B	109.3	C7A—C8A—C3A	117 (2)
H12A—C12—H12B	108	C7A—C8A—C9A	137 (2)
N13—C16—C17	113.32 (17)	C3A—C8A—C9A	105 (2)
N13—C16—H16A	108.9	N1A—C9A—C8A	110 (2)
C17—C16—H16A	108.9	N1A—C9A—C10	116 (3)
N13—C16—H16B	108.9	C8A—C9A—C10	133 (3)
C17—C16—H16B	108.9	C25—C26—C27	120.0 (3)
H16A—C16—H16B	107.7	C25—C26—C28A	133.7 (6)
C14—C15—C10	111.13 (18)	C27—C26—C28A	104.4 (7)
C14—C15—H15A	109.4	C25—C26—H26	118.3 (13)
C10—C15—H15A	109.4	C27—C26—H26	119.8 (13)
C14—C15—H15B	109.4	C28A—C26—H26	32 (2)
C10—C15—H15B	109.4	C24—C28—H28A	109.5
H15A—C15—H15B	108	C24—C28—H28B	109.5
C27—C22—C23	121.3 (2)	H28A—C28—H28B	109.5
C27—C22—S21	119.2 (2)	C24—C28—H28C	109.5
C23—C22—S21	119.43 (19)	H28A—C28—H28C	109.5
N13—C14—C15	110.60 (19)	H28B—C28—H28C	109.5
N13—C14—H14A	109.5	C24—C28—H24	28 (7)
C15—C14—H14A	109.5	H28A—C28—H24	104.9
N13—C14—H14B	109.5	H28B—C28—H24	86.4
C15—C14—H14B	109.5	H28C—C28—H24	133.8
H14A—C14—H14B	108.1	C23—C24—C25	117.0 (3)
C12—C11—C10	112.3 (2)	C23—C24—C28	119.5 (3)
C12—C11—H11A	109.2	C25—C24—C28	123.4 (3)
C10—C11—H11A	109.2	C23—C24—H24	120 (2)
C12—C11—H11B	109.2	C25—C24—H24	119 (2)
C10—C11—H11B	109.2	C28—C24—H24	21 (7)
H11A—C11—H11B	107.9	C26—C28A—H28D	109.5
C24—C23—C22	121.2 (3)	C26—C28A—H28E	109.5
C24—C23—H23	119.4	H28D—C28A—H28E	109.5
C22—C23—H23	119.4	C26—C28A—H28F	109.5
C22—C27—C26	117.8 (3)	H28D—C28A—H28F	109.5
C22—C27—H27	121.1	H28E—C28A—H28F	109.5
C26—C27—H27	121.1	C26—C28A—H26	28.5 (14)
C26—C25—C24	122.5 (3)	H28D—C28A—H26	97.9
C26—C25—H25	118.8	H28E—C28A—H26	137.4
C24—C25—H25	118.8	H28F—C28A—H26	90.3
C9—N1—O2	107.3 (5)
O21B—S21—N20—C18	−178.60 (16)	C6—C7—C8—C9	−178.9 (5)
O21A—S21—N20—C18	−48.72 (19)	O2—N1—C9—C8	−0.4 (4)
C22—S21—N20—C18	66.76 (19)	O2—N1—C9—C10	176.7 (3)
S21—N20—C18—C17	143.00 (16)	C3—C8—C9—N1	1.1 (4)
C16—C17—C18—N20	−67.4 (2)	C7—C8—C9—N1	−179.6 (5)
C14—N13—C12—C11	−56.2 (2)	C3—C8—C9—C10	−175.6 (3)
C16—N13—C12—C11	178.79 (18)	C7—C8—C9—C10	3.7 (7)
C14—N13—C16—C17	64.7 (2)	C15—C10—C9—N1	113.6 (3)
C12—N13—C16—C17	−171.62 (18)	C11—C10—C9—N1	−123.8 (3)
C18—C17—C16—N13	−179.03 (18)	C15—C10—C9—C8	−69.8 (4)
C9—C10—C15—C14	−179.6 (3)	C11—C10—C9—C8	52.7 (4)
C11—C10—C15—C14	55.7 (3)	C9A—N1A—O2A—C3A	−3 (3)
C9A—C10—C15—C14	170.1 (15)	N1A—O2A—C3A—C4A	−178 (2)
O21B—S21—C22—C27	−28.6 (2)	N1A—O2A—C3A—C8A	3 (3)
O21A—S21—C22—C27	−157.5 (2)	O2A—C3A—C4A—C5A	178 (2)
N20—S21—C22—C27	85.9 (2)	C8A—C3A—C4A—C5A	−4 (4)
O21B—S21—C22—C23	150.2 (2)	C3A—C4A—C5A—C6A	3 (4)
O21A—S21—C22—C23	21.3 (2)	C3A—C4A—C5A—F5A	−178 (2)
N20—S21—C22—C23	−95.3 (2)	F5A—C5A—C6A—C7A	178 (2)
C16—N13—C14—C15	−178.03 (17)	C4A—C5A—C6A—C7A	−3 (5)
C12—N13—C14—C15	58.9 (2)	C5A—C6A—C7A—C8A	3 (4)
C10—C15—C14—N13	−59.5 (2)	C6A—C7A—C8A—C3A	−4 (3)
N13—C12—C11—C10	54.1 (3)	C6A—C7A—C8A—C9A	−177 (3)
C9—C10—C11—C12	−176.3 (3)	C4A—C3A—C8A—C7A	5 (4)
C15—C10—C11—C12	−53.1 (2)	O2A—C3A—C8A—C7A	−176.6 (19)
C9A—C10—C11—C12	177.6 (14)	C4A—C3A—C8A—C9A	180 (3)
C27—C22—C23—C24	1.5 (4)	O2A—C3A—C8A—C9A	−2 (3)
S21—C22—C23—C24	−177.2 (2)	O2A—N1A—C9A—C8A	2 (3)
C23—C22—C27—C26	−2.6 (4)	O2A—N1A—C9A—C10	−173.7 (18)
S21—C22—C27—C26	176.2 (3)	C7A—C8A—C9A—N1A	173 (3)
C9—N1—O2—C3	−0.5 (4)	C3A—C8A—C9A—N1A	0 (3)
N1—O2—C3—C8	1.2 (5)	C7A—C8A—C9A—C10	−12 (5)
N1—O2—C3—C4	−178.7 (5)	C3A—C8A—C9A—C10	175 (2)
O2—C3—C4—C5	−179.5 (6)	C15—C10—C9A—N1A	112 (2)
C8—C3—C4—C5	0.6 (9)	C11—C10—C9A—N1A	−128 (2)
C3—C4—C5—F5	−179.2 (6)	C15—C10—C9A—C8A	−63 (3)
C3—C4—C5—C6	0.4 (11)	C11—C10—C9A—C8A	57 (3)
C4—C5—C6—C7	−1.0 (11)	C24—C25—C26—C27	2.4 (6)
F5—C5—C6—C7	178.6 (6)	C24—C25—C26—C28A	−158.9 (11)
C5—C6—C7—C8	0.6 (8)	C22—C27—C26—C25	0.7 (5)
O2—C3—C8—C7	179.1 (4)	C22—C27—C26—C28A	166.8 (8)
C4—C3—C8—C7	−0.9 (7)	C22—C23—C24—C25	1.5 (4)
O2—C3—C8—C9	−1.4 (5)	C22—C23—C24—C28	−176.9 (3)
C4—C3—C8—C9	178.6 (5)	C26—C25—C24—C23	−3.4 (5)
C6—C7—C8—C3	0.3 (7)	C26—C25—C24—C28	174.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13···Cl1	0.90 (3)	2.17 (3)	3.0727 (18)	174 (2)
N20—H20···Cl1^i	0.87 (3)	2.30 (3)	3.145 (2)	165 (2)
C15—H15A···Cl1^ii	0.99	2.72	3.632 (2)	153
C17—H17B···Cl1^iii	0.99	2.79	3.733 (2)	160
C12—H12A···O21A^iv	0.99	2.65	3.373 (3)	130
C12—H12B···O21B^v	0.99	2.52	3.499 (3)	171
C16—H16A···O21B^ii	0.99	2.41	3.206 (3)	137
C16—H16B···O21A^iv	0.99	2.46	3.288 (3)	141
C4A—H4A···O2A^vi	0.95	2.56	3.47 (4)	160

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) x, y+1, z; (iii) −x+1/2, y+1/2, −z+1/2; (iv) −x, y, −z+1/2; (v) −x, y+1, −z+1/2; (vi) −x+1/2, −y+5/2, −z+1.

4-(6-Fluoro-1,2-benzoxazol-3-yl)-1-[4-(5-fluoro-3-methylbenzo[b]thiophene-2-sulfonamido)butyl]piperidin-1-ium chloride (II)

Crystal data

C25H28F2N3O3S2^+·Cl^−	F(000) = 1160
Mr = 556.07	Dx = 1.472 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 17964 reflections
a = 5.9960 (1) Å	θ = 3.2–78.3°
b = 41.1095 (5) Å	µ = 3.33 mm^−1
c = 10.4904 (2) Å	T = 120 K
β = 103.972 (2)°	Plate, white
V = 2509.30 (7) Å^3	0.45 × 0.2 × 0.05 mm
Z = 4

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	5288 independent reflections
Mirror monochromator	4690 reflections with I > 2σ(I)
Detector resolution: 10.3756 pixels mm^-1	Rint = 0.062
ω scans	θmax = 78.6°, θmin = 4.3°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −7→7
Tmin = 0.314, Tmax = 1	k = −51→51
50888 measured reflections	l = −11→13

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 1.8028P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
5288 reflections	Δρmax = 0.30 e Å^−3
333 parameters	Δρmin = −0.44 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	Occ. (<1)
N1	0.3469 (3)	0.38338 (4)	0.41884 (16)	0.0227 (3)
O2	0.2279 (2)	0.41382 (3)	0.38971 (14)	0.0243 (3)
C3	0.3355 (3)	0.43088 (4)	0.31132 (19)	0.0222 (4)
C4	0.2709 (3)	0.46140 (5)	0.2570 (2)	0.0278 (4)
H4	0.144	0.4733	0.2726	0.033*
C5	0.4073 (4)	0.47270 (4)	0.1793 (2)	0.0304 (5)
F5	0.3540 (2)	0.50229 (3)	0.12117 (15)	0.0423 (3)
C6	0.5959 (4)	0.45640 (5)	0.1535 (2)	0.0292 (4)
H6	0.6822	0.4659	0.0982	0.035*
C7	0.6554 (3)	0.42605 (5)	0.20984 (19)	0.0247 (4)
H7	0.7834	0.4144	0.1948	0.03*
C8	0.5210 (3)	0.41336 (4)	0.28917 (18)	0.0201 (4)
C9	0.5150 (3)	0.38359 (4)	0.36059 (17)	0.0189 (3)
C10	0.6725 (3)	0.35479 (4)	0.36966 (18)	0.0191 (3)
H10	0.7589	0.3571	0.2997	0.023*
C11	0.8489 (3)	0.35309 (4)	0.50310 (18)	0.0200 (3)
H11A	0.9462	0.3728	0.5155	0.024*
H11B	0.7676	0.3522	0.5747	0.024*
C12	0.9991 (3)	0.32305 (4)	0.50872 (19)	0.0209 (4)
H12A	1.0854	0.3243	0.4394	0.025*
H12B	1.1113	0.3219	0.595	0.025*
N13	0.8501 (2)	0.29320 (3)	0.48882 (15)	0.0176 (3)
C14	0.6905 (3)	0.29374 (4)	0.35501 (19)	0.0221 (4)
H14A	0.5975	0.2736	0.3406	0.027*
H14B	0.78	0.2949	0.2872	0.027*
C15	0.5339 (3)	0.32319 (4)	0.34434 (19)	0.0224 (4)
H15A	0.4385	0.3212	0.4089	0.027*
H15B	0.4296	0.3239	0.2555	0.027*
C16	0.9798 (3)	0.26172 (4)	0.52098 (19)	0.0209 (4)
H16A	0.8681	0.2442	0.524	0.025*
H16B	1.0832	0.2636	0.6098	0.025*
C17	1.1217 (3)	0.25179 (4)	0.42587 (19)	0.0212 (4)
H17A	1.2323	0.2693	0.4201	0.025*
H17B	1.0196	0.2486	0.3373	0.025*
C18	1.2530 (3)	0.22010 (4)	0.47179 (19)	0.0216 (4)
H18A	1.4	0.2205	0.4446	0.026*
H18B	1.2902	0.2194	0.569	0.026*
C19	1.1234 (3)	0.18911 (4)	0.41868 (19)	0.0217 (4)
H19A	1.0978	0.1888	0.3219	0.026*
H19B	1.2197	0.1701	0.4539	0.026*
N20	0.8990 (3)	0.18602 (4)	0.45308 (16)	0.0195 (3)
S21	0.84895 (7)	0.15446 (2)	0.53242 (4)	0.01825 (10)
O21A	0.6165 (2)	0.15725 (3)	0.54481 (13)	0.0241 (3)
O21B	1.0326 (2)	0.15125 (3)	0.64862 (13)	0.0244 (3)
C22	0.8704 (3)	0.11991 (4)	0.43722 (18)	0.0187 (3)
S23	1.12214 (8)	0.09738 (2)	0.48311 (5)	0.02286 (11)
C24	1.0334 (3)	0.07323 (4)	0.34468 (19)	0.0235 (4)
C25	1.1618 (4)	0.04850 (5)	0.3047 (2)	0.0296 (4)
H25	1.3092	0.0427	0.3567	0.035*
C26	1.0684 (4)	0.03276 (5)	0.1879 (2)	0.0338 (5)
H26	1.1527	0.0163	0.1567	0.041*
C27	0.8491 (4)	0.04131 (5)	0.1164 (2)	0.0321 (5)
F27	0.7611 (3)	0.02477 (3)	0.00290 (14)	0.0483 (4)
C28	0.7188 (4)	0.06524 (5)	0.1529 (2)	0.0270 (4)
H28	0.5693	0.0702	0.1014	0.032*
C29	0.8146 (3)	0.08223 (4)	0.26959 (18)	0.0214 (4)
C30	0.7202 (3)	0.10975 (4)	0.32469 (18)	0.0190 (3)
C31	0.4918 (3)	0.12477 (5)	0.26257 (19)	0.0229 (4)
H31A	0.4193	0.1127	0.1827	0.034*	0.5
H31B	0.3927	0.1239	0.3244	0.034*	0.5
H31C	0.514	0.1475	0.2401	0.034*	0.5
H31D	0.4647	0.1433	0.3154	0.034*	0.5
H31E	0.4913	0.1322	0.1737	0.034*	0.5
H31F	0.37	0.1086	0.258	0.034*	0.5
Cl1	0.56190 (7)	0.28677 (2)	0.69293 (4)	0.02109 (10)
H13	0.762 (4)	0.2944 (5)	0.551 (2)	0.021 (5)*
H20	0.790 (5)	0.1909 (6)	0.393 (3)	0.038 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0248 (8)	0.0209 (7)	0.0227 (8)	0.0056 (6)	0.0067 (6)	0.0024 (6)
O2	0.0243 (6)	0.0231 (6)	0.0265 (7)	0.0063 (5)	0.0078 (5)	0.0022 (5)
C3	0.0219 (8)	0.0226 (9)	0.0202 (9)	0.0000 (7)	0.0016 (7)	−0.0008 (7)
C4	0.0273 (9)	0.0210 (9)	0.0315 (11)	0.0027 (7)	−0.0002 (8)	−0.0007 (8)
C5	0.0348 (11)	0.0182 (9)	0.0320 (11)	−0.0020 (7)	−0.0038 (9)	0.0046 (8)
F5	0.0482 (8)	0.0231 (6)	0.0517 (9)	0.0010 (5)	0.0046 (6)	0.0153 (6)
C6	0.0308 (10)	0.0279 (10)	0.0276 (11)	−0.0068 (8)	0.0046 (8)	0.0062 (8)
C7	0.0240 (9)	0.0260 (9)	0.0226 (10)	−0.0021 (7)	0.0027 (7)	0.0012 (7)
C8	0.0213 (8)	0.0197 (8)	0.0178 (9)	0.0003 (6)	0.0015 (7)	0.0005 (6)
C9	0.0206 (8)	0.0206 (8)	0.0146 (9)	0.0005 (6)	0.0027 (6)	0.0002 (6)
C10	0.0205 (8)	0.0198 (8)	0.0181 (9)	0.0026 (6)	0.0067 (7)	0.0016 (6)
C11	0.0182 (8)	0.0199 (8)	0.0216 (9)	0.0005 (6)	0.0043 (7)	−0.0018 (7)
C12	0.0165 (8)	0.0211 (8)	0.0238 (10)	−0.0002 (6)	0.0025 (7)	0.0000 (7)
N13	0.0176 (7)	0.0196 (7)	0.0172 (8)	0.0016 (5)	0.0070 (6)	0.0009 (5)
C14	0.0210 (8)	0.0217 (8)	0.0219 (10)	0.0013 (6)	0.0017 (7)	−0.0031 (7)
C15	0.0189 (8)	0.0224 (8)	0.0238 (10)	0.0015 (7)	0.0009 (7)	−0.0024 (7)
C16	0.0223 (8)	0.0203 (8)	0.0211 (10)	0.0043 (6)	0.0071 (7)	0.0029 (7)
C17	0.0212 (8)	0.0211 (8)	0.0231 (10)	0.0015 (6)	0.0087 (7)	0.0014 (7)
C18	0.0180 (8)	0.0219 (8)	0.0250 (10)	0.0022 (6)	0.0056 (7)	−0.0006 (7)
C19	0.0218 (8)	0.0219 (8)	0.0231 (10)	0.0018 (7)	0.0085 (7)	−0.0015 (7)
N20	0.0179 (7)	0.0211 (7)	0.0192 (8)	0.0018 (5)	0.0039 (6)	0.0013 (6)
S21	0.0173 (2)	0.0231 (2)	0.0143 (2)	0.00120 (14)	0.00367 (15)	−0.00109 (15)
O21A	0.0193 (6)	0.0314 (7)	0.0228 (7)	0.0009 (5)	0.0072 (5)	−0.0025 (5)
O21B	0.0225 (6)	0.0339 (7)	0.0150 (7)	0.0025 (5)	0.0009 (5)	−0.0008 (5)
C22	0.0206 (8)	0.0198 (8)	0.0165 (9)	0.0020 (6)	0.0062 (7)	0.0018 (6)
S23	0.0217 (2)	0.0231 (2)	0.0221 (2)	0.00437 (15)	0.00199 (17)	0.00030 (16)
C24	0.0273 (9)	0.0207 (8)	0.0231 (10)	0.0024 (7)	0.0075 (8)	0.0013 (7)
C25	0.0309 (10)	0.0253 (9)	0.0326 (12)	0.0079 (8)	0.0078 (9)	−0.0003 (8)
C26	0.0447 (12)	0.0236 (9)	0.0350 (12)	0.0094 (8)	0.0130 (10)	−0.0025 (8)
C27	0.0475 (12)	0.0238 (9)	0.0236 (11)	0.0036 (8)	0.0060 (9)	−0.0053 (8)
F27	0.0678 (10)	0.0371 (7)	0.0326 (8)	0.0142 (7)	−0.0020 (7)	−0.0159 (6)
C28	0.0349 (10)	0.0229 (9)	0.0211 (10)	0.0029 (7)	0.0025 (8)	−0.0007 (7)
C29	0.0262 (9)	0.0183 (8)	0.0202 (9)	0.0002 (7)	0.0068 (7)	0.0014 (7)
C30	0.0213 (8)	0.0195 (8)	0.0172 (9)	−0.0005 (6)	0.0066 (7)	0.0023 (6)
C31	0.0222 (9)	0.0261 (9)	0.0191 (9)	0.0021 (7)	0.0023 (7)	−0.0007 (7)
Cl1	0.01978 (19)	0.0257 (2)	0.0180 (2)	−0.00133 (15)	0.00501 (15)	−0.00023 (15)

Geometric parameters (Å, º)

N1—C9	1.299 (2)	C17—C18	1.538 (2)
N1—O2	1.4366 (18)	C17—H17A	0.99
O2—C3	1.357 (2)	C17—H17B	0.99
C3—C8	1.391 (3)	C18—C19	1.525 (2)
C3—C4	1.393 (3)	C18—H18A	0.99
C4—C5	1.368 (3)	C18—H18B	0.99
C4—H4	0.95	C19—N20	1.480 (2)
C5—F5	1.364 (2)	C19—H19A	0.99
C5—C6	1.396 (3)	C19—H19B	0.99
C6—C7	1.390 (3)	N20—S21	1.6086 (16)
C6—H6	0.95	N20—H20	0.82 (3)
C7—C8	1.392 (3)	S21—O21A	1.4355 (13)
C7—H7	0.95	S21—O21B	1.4379 (13)
C8—C9	1.440 (2)	S21—C22	1.7587 (18)
C9—C10	1.503 (2)	C22—C30	1.366 (3)
C10—C15	1.530 (2)	C22—S23	1.7371 (17)
C10—C11	1.539 (2)	S23—C24	1.733 (2)
C10—H10	1	C24—C25	1.399 (3)
C11—C12	1.521 (2)	C24—C29	1.407 (3)
C11—H11A	0.99	C25—C26	1.379 (3)
C11—H11B	0.99	C25—H25	0.95
C12—N13	1.502 (2)	C26—C27	1.393 (3)
C12—H12A	0.99	C26—H26	0.95
C12—H12B	0.99	C27—F27	1.362 (2)
N13—C14	1.496 (2)	C27—C28	1.368 (3)
N13—C16	1.505 (2)	C28—C29	1.406 (3)
N13—H13	0.94 (2)	C28—H28	0.95
C14—C15	1.520 (2)	C29—C30	1.447 (2)
C14—H14A	0.99	C30—C31	1.501 (2)
C14—H14B	0.99	C31—H31A	0.98
C15—H15A	0.99	C31—H31B	0.98
C15—H15B	0.99	C31—H31C	0.98
C16—C17	1.515 (2)	C31—H31D	0.98
C16—H16A	0.99	C31—H31E	0.98
C16—H16B	0.99	C31—H31F	0.98
C9—N1—O2	107.22 (14)	C18—C17—H17B	109.6
C3—O2—N1	107.15 (13)	H17A—C17—H17B	108.1
O2—C3—C8	110.48 (16)	C19—C18—C17	114.58 (15)
O2—C3—C4	125.97 (18)	C19—C18—H18A	108.6
C8—C3—C4	123.54 (19)	C17—C18—H18A	108.6
C5—C4—C3	113.73 (19)	C19—C18—H18B	108.6
C5—C4—H4	123.1	C17—C18—H18B	108.6
C3—C4—H4	123.1	H18A—C18—H18B	107.6
F5—C5—C4	117.43 (19)	N20—C19—C18	113.29 (15)
F5—C5—C6	117.0 (2)	N20—C19—H19A	108.9
C4—C5—C6	125.53 (18)	C18—C19—H19A	108.9
C7—C6—C5	119.06 (19)	N20—C19—H19B	108.9
C7—C6—H6	120.5	C18—C19—H19B	108.9
C5—C6—H6	120.5	H19A—C19—H19B	107.7
C6—C7—C8	117.65 (18)	C19—N20—S21	119.32 (12)
C6—C7—H7	121.2	C19—N20—H20	113.1 (19)
C8—C7—H7	121.2	S21—N20—H20	112.6 (19)
C3—C8—C7	120.49 (17)	O21A—S21—O21B	119.48 (8)
C3—C8—C9	103.41 (16)	O21A—S21—N20	106.80 (8)
C7—C8—C9	136.08 (17)	O21B—S21—N20	108.19 (8)
N1—C9—C8	111.73 (16)	O21A—S21—C22	108.76 (8)
N1—C9—C10	120.80 (16)	O21B—S21—C22	105.16 (8)
C8—C9—C10	127.46 (16)	N20—S21—C22	108.02 (8)
C9—C10—C15	110.54 (14)	C30—C22—S23	115.08 (13)
C9—C10—C11	112.13 (15)	C30—C22—S21	127.92 (14)
C15—C10—C11	110.15 (14)	S23—C22—S21	116.80 (10)
C9—C10—H10	108	C24—S23—C22	90.16 (9)
C15—C10—H10	108	C25—C24—C29	121.96 (18)
C11—C10—H10	108	C25—C24—S23	125.97 (16)
C12—C11—C10	110.04 (15)	C29—C24—S23	112.00 (14)
C12—C11—H11A	109.7	C26—C25—C24	118.20 (19)
C10—C11—H11A	109.7	C26—C25—H25	120.9
C12—C11—H11B	109.7	C24—C25—H25	120.9
C10—C11—H11B	109.7	C25—C26—C27	119.22 (19)
H11A—C11—H11B	108.2	C25—C26—H26	120.4
N13—C12—C11	109.34 (14)	C27—C26—H26	120.4
N13—C12—H12A	109.8	F27—C27—C28	118.5 (2)
C11—C12—H12A	109.8	F27—C27—C26	117.47 (19)
N13—C12—H12B	109.8	C28—C27—C26	124.04 (19)
C11—C12—H12B	109.8	C27—C28—C29	117.39 (19)
H12A—C12—H12B	108.3	C27—C28—H28	121.3
C14—N13—C12	110.02 (14)	C29—C28—H28	121.3
C14—N13—C16	113.69 (14)	C28—C29—C24	119.13 (17)
C12—N13—C16	114.43 (13)	C28—C29—C30	128.27 (17)
C14—N13—H13	108.3 (14)	C24—C29—C30	112.57 (16)
C12—N13—H13	106.1 (13)	C22—C30—C29	110.17 (16)
C16—N13—H13	103.7 (13)	C22—C30—C31	126.29 (16)
N13—C14—C15	108.96 (15)	C29—C30—C31	123.53 (16)
N13—C14—H14A	109.9	C30—C31—H31A	109.5
C15—C14—H14A	109.9	C30—C31—H31B	109.5
N13—C14—H14B	109.9	H31A—C31—H31B	109.5
C15—C14—H14B	109.9	C30—C31—H31C	109.5
H14A—C14—H14B	108.3	H31A—C31—H31C	109.5
C14—C15—C10	111.31 (14)	H31B—C31—H31C	109.5
C14—C15—H15A	109.4	C30—C31—H31D	109.5
C10—C15—H15A	109.4	H31A—C31—H31D	141.1
C14—C15—H15B	109.4	H31B—C31—H31D	56.3
C10—C15—H15B	109.4	H31C—C31—H31D	56.3
H15A—C15—H15B	108	C30—C31—H31E	109.5
N13—C16—C17	115.19 (15)	H31A—C31—H31E	56.3
N13—C16—H16A	108.5	H31B—C31—H31E	141.1
C17—C16—H16A	108.5	H31C—C31—H31E	56.3
N13—C16—H16B	108.5	H31D—C31—H31E	109.5
C17—C16—H16B	108.5	C30—C31—H31F	109.5
H16A—C16—H16B	107.5	H31A—C31—H31F	56.3
C16—C17—C18	110.37 (15)	H31B—C31—H31F	56.3
C16—C17—H17A	109.6	H31C—C31—H31F	141.1
C18—C17—H17A	109.6	H31D—C31—H31F	109.5
C16—C17—H17B	109.6	H31E—C31—H31F	109.5
C9—N1—O2—C3	0.69 (19)	N13—C16—C17—C18	177.81 (14)
N1—O2—C3—C8	−0.8 (2)	C16—C17—C18—C19	90.21 (19)
N1—O2—C3—C4	177.97 (18)	C17—C18—C19—N20	−58.1 (2)
O2—C3—C4—C5	−178.67 (18)	C18—C19—N20—S21	−122.75 (15)
C8—C3—C4—C5	0.0 (3)	C19—N20—S21—O21A	−176.74 (13)
C3—C4—C5—F5	179.28 (17)	C19—N20—S21—O21B	53.45 (16)
C3—C4—C5—C6	−0.2 (3)	C19—N20—S21—C22	−59.90 (16)
F5—C5—C6—C7	−179.51 (18)	O21A—S21—C22—C30	42.95 (19)
C4—C5—C6—C7	0.0 (3)	O21B—S21—C22—C30	172.04 (16)
C5—C6—C7—C8	0.4 (3)	N20—S21—C22—C30	−72.61 (18)
O2—C3—C8—C7	179.26 (16)	O21A—S21—C22—S23	−142.50 (10)
C4—C3—C8—C7	0.4 (3)	O21B—S21—C22—S23	−13.41 (13)
O2—C3—C8—C9	0.7 (2)	N20—S21—C22—S23	101.95 (11)
C4—C3—C8—C9	−178.18 (17)	C30—C22—S23—C24	1.47 (15)
C6—C7—C8—C3	−0.6 (3)	S21—C22—S23—C24	−173.79 (11)
C6—C7—C8—C9	177.4 (2)	C22—S23—C24—C25	175.61 (19)
O2—N1—C9—C8	−0.3 (2)	C22—S23—C24—C29	−1.50 (15)
O2—N1—C9—C10	−179.02 (15)	C29—C24—C25—C26	0.1 (3)
C3—C8—C9—N1	−0.2 (2)	S23—C24—C25—C26	−176.78 (16)
C7—C8—C9—N1	−178.5 (2)	C24—C25—C26—C27	−1.8 (3)
C3—C8—C9—C10	178.42 (17)	C25—C26—C27—F27	−178.7 (2)
C7—C8—C9—C10	0.2 (3)	C25—C26—C27—C28	1.6 (4)
N1—C9—C10—C15	46.4 (2)	F27—C27—C28—C29	−179.25 (18)
C8—C9—C10—C15	−132.10 (18)	C26—C27—C28—C29	0.5 (3)
N1—C9—C10—C11	−76.9 (2)	C27—C28—C29—C24	−2.2 (3)
C8—C9—C10—C11	104.6 (2)	C27—C28—C29—C30	175.43 (19)
C9—C10—C11—C12	178.33 (15)	C25—C24—C29—C28	2.0 (3)
C15—C10—C11—C12	54.78 (19)	S23—C24—C29—C28	179.22 (15)
C10—C11—C12—N13	−58.92 (19)	C25—C24—C29—C30	−176.00 (18)
C11—C12—N13—C14	63.14 (18)	S23—C24—C29—C30	1.3 (2)
C11—C12—N13—C16	−167.42 (15)	S23—C22—C30—C29	−1.0 (2)
C12—N13—C14—C15	−62.11 (18)	S21—C22—C30—C29	173.63 (13)
C16—N13—C14—C15	168.06 (15)	S23—C22—C30—C31	−179.71 (14)
N13—C14—C15—C10	58.1 (2)	S21—C22—C30—C31	−5.1 (3)
C9—C10—C15—C14	−179.20 (15)	C28—C29—C30—C22	−177.91 (19)
C11—C10—C15—C14	−54.7 (2)	C24—C29—C30—C22	−0.2 (2)
C14—N13—C16—C17	57.0 (2)	C28—C29—C30—C31	0.8 (3)
C12—N13—C16—C17	−70.6 (2)	C24—C29—C30—C31	178.58 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13···Cl1	0.94 (2)	2.15 (2)	3.0706 (16)	168.7 (19)
N20—H20···Cl1^i	0.82 (3)	2.39 (3)	3.1814 (16)	163 (3)
C14—H14A···Cl1^i	0.99	2.91	3.7157 (18)	140
C6—H6···F5^ii	0.95	2.61	3.420 (2)	143
C25—H25···F5^iii	0.95	2.58	3.399 (2)	144
C26—H26···F27^iv	0.95	2.52	3.411 (2)	157
C16—H16A···N20	0.99	2.52	3.203 (2)	126
C10—H10···O21B^i	1	2.56	3.538 (2)	164
C15—H15B···O21B^v	0.99	2.58	3.373 (2)	137
C19—H19B···O21A^vi	0.99	2.4	3.212 (2)	139

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

4-(6-Fluoro-1,2-benzoxazol-3-yl)-1-[4-(6-fluorobenzo[b]thiophene-2-sulfonamido)butyl]piperidin-1-ium chloride (III)

Crystal data

C24H26ClFN3O3S2^+·Cl^−	F(000) = 1160
Mr = 558.5	Dx = 1.453 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 17400 reflections
a = 21.8891 (3) Å	θ = 3.9–71.0°
b = 6.9580 (1) Å	µ = 4.16 mm^−1
c = 17.7899 (2) Å	T = 120 K
β = 109.558 (1)°	Prism, white
V = 2553.15 (6) Å^3	0.5 × 0.2 × 0.1 mm
Z = 4

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	4938 independent reflections
Mirror monochromator	4478 reflections with I > 2σ(I)
Detector resolution: 10.3756 pixels mm^-1	Rint = 0.033
ω scans	θmax = 71.2°, θmin = 4.3°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −26→26
Tmin = 0.386, Tmax = 1	k = −8→8
35525 measured reflections	l = −21→21

Refinement

Refinement on F^2	19 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.071	w = 1/[σ^2(Fo^2) + (0.0331P)^2 + 1.1748P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
4938 reflections	Δρmax = 0.29 e Å^−3
361 parameters	Δρmin = −0.35 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	Occ. (<1)
N1	0.19348 (6)	0.5498 (2)	0.13233 (9)	0.0364 (3)
O2	0.13067 (5)	0.52025 (16)	0.13932 (7)	0.0380 (3)
C3	0.11337 (7)	0.6871 (2)	0.16615 (9)	0.0312 (3)
C4	0.05492 (8)	0.7236 (3)	0.17811 (9)	0.0370 (4)
H4	0.0216	0.63	0.1692	0.044*
C5	0.04950 (7)	0.9060 (3)	0.20384 (9)	0.0382 (4)
F5	−0.00637 (5)	0.95044 (18)	0.21757 (6)	0.0524 (3)
C6	0.09626 (8)	1.0489 (3)	0.21701 (10)	0.0392 (4)
H6	0.0888	1.1728	0.2347	0.047*
C7	0.15380 (7)	1.0086 (2)	0.20407 (9)	0.0327 (3)
H7	0.1866	1.1034	0.2123	0.039*
C8	0.16199 (7)	0.8229 (2)	0.17841 (8)	0.0273 (3)
C9	0.21065 (7)	0.7251 (2)	0.15535 (9)	0.0279 (3)
C10	0.27493 (7)	0.8028 (2)	0.15686 (8)	0.0260 (3)
H10	0.2737	0.9461	0.1604	0.031*
C11	0.32978 (7)	0.7280 (2)	0.22964 (8)	0.0259 (3)
H11A	0.3206	0.7607	0.279	0.031*
H11B	0.3326	0.5864	0.2266	0.031*
C12	0.39357 (7)	0.8178 (2)	0.23210 (8)	0.0254 (3)
H12A	0.391	0.9591	0.2368	0.031*
H12B	0.4288	0.7702	0.2795	0.031*
N13	0.40898 (5)	0.76947 (17)	0.15817 (7)	0.0215 (2)
C14	0.35560 (7)	0.8337 (2)	0.08465 (8)	0.0245 (3)
H14A	0.3655	0.7923	0.0367	0.029*
H14B	0.3529	0.9757	0.084	0.029*
C15	0.29089 (7)	0.7498 (2)	0.08207 (8)	0.0262 (3)
H15A	0.2923	0.6082	0.0776	0.031*
H15B	0.2563	0.7988	0.0343	0.031*
C16	0.47344 (6)	0.8532 (2)	0.16411 (8)	0.0242 (3)
H16A	0.5045	0.8242	0.2178	0.029*
H16B	0.4689	0.9947	0.1595	0.029*
C17	0.50225 (7)	0.7831 (2)	0.10245 (8)	0.0253 (3)
H17A	0.4717	0.8065	0.0479	0.03*
H17B	0.5114	0.6436	0.1089	0.03*
C18	0.56511 (7)	0.8955 (2)	0.11599 (9)	0.0280 (3)
H18A	0.5554	1.0345	0.1161	0.034*
H18B	0.5957	0.8628	0.1695	0.034*
C19	0.59854 (7)	0.8599 (2)	0.05514 (9)	0.0283 (3)
H19A	0.568	0.8918	0.0015	0.034*
H19B	0.636	0.948	0.0664	0.034*
N20	0.62154 (6)	0.66071 (18)	0.05396 (8)	0.0270 (3)
S21	0.69073 (2)	0.59582 (5)	0.11680 (2)	0.02611 (9)
O21B	0.69061 (5)	0.64403 (16)	0.19518 (6)	0.0329 (2)
O21A	0.70102 (5)	0.40158 (15)	0.09710 (6)	0.0328 (2)
Cl1	0.41227 (2)	0.33779 (5)	0.13379 (2)	0.03324 (10)
C22	0.75210 (10)	0.7345 (3)	0.10021 (13)	0.0249 (4)	0.9468 (12)
S23	0.77279 (2)	0.95669 (7)	0.14691 (3)	0.03092 (14)	0.9468 (12)
C24	0.82756 (9)	0.9950 (2)	0.09684 (11)	0.0291 (4)	0.9468 (12)
C25	0.86570 (9)	1.1589 (3)	0.10149 (10)	0.0355 (4)	0.9468 (12)
H25	0.8637	1.2655	0.1339	0.043*	0.9468 (12)
C26	0.90639 (13)	1.1580 (4)	0.05666 (12)	0.0366 (5)	0.9468 (12)
Cl26	0.95528 (3)	1.35655 (8)	0.05935 (3)	0.05927 (18)	0.9468 (12)
C27	0.90973 (8)	1.0044 (3)	0.00763 (10)	0.0385 (4)	0.9468 (12)
H27	0.9382	1.0107	−0.0226	0.046*	0.9468 (12)
C28	0.87184 (8)	0.8438 (3)	0.00306 (10)	0.0356 (4)	0.9468 (12)
H28	0.8741	0.7385	−0.0299	0.043*	0.9468 (12)
C29	0.82969 (9)	0.8376 (2)	0.04788 (11)	0.0288 (4)	0.9468 (12)
C30	0.7866 (2)	0.6890 (5)	0.0497 (3)	0.0283 (4)	0.9468 (12)
H30	0.7818	0.5728	0.0202	0.034*	0.9468 (12)
C22A	0.746 (2)	0.772 (5)	0.111 (3)	0.0249 (4)	0.0532 (12)
S23A	0.7857 (14)	0.689 (3)	0.049 (2)	0.05927 (18)	0.0532 (12)
C24A	0.8317 (16)	0.897 (4)	0.060 (2)	0.0291 (4)	0.0532 (12)
C25A	0.8802 (14)	0.936 (4)	0.0258 (18)	0.0355 (4)	0.0532 (12)
H25A	0.8966	0.8454	−0.0025	0.043*	0.0532 (12)
C26A	0.900 (3)	1.127 (5)	0.040 (3)	0.0366 (5)	0.0532 (12)
Cl2A	0.9700 (4)	1.2212 (13)	0.0187 (5)	0.047 (2)	0.0532 (12)
C27A	0.8885 (14)	1.247 (6)	0.0971 (18)	0.0385 (4)	0.0532 (12)
H27A	0.9133	1.3608	0.1128	0.046*	0.0532 (12)
C28A	0.8414 (14)	1.204 (4)	0.1318 (18)	0.0356 (4)	0.0532 (12)
H28A	0.8289	1.2901	0.1654	0.043*	0.0532 (12)
C29A	0.8145 (17)	1.020 (4)	0.112 (2)	0.0288 (4)	0.0532 (12)
C30A	0.7603 (18)	0.965 (5)	0.131 (3)	0.0283 (4)	0.0532 (12)
H30A	0.7368	1.0465	0.1548	0.034*	0.0532 (12)
H13	0.4109 (8)	0.639 (3)	0.1540 (10)	0.029 (4)*
H20	0.6179 (9)	0.622 (3)	0.0073 (12)	0.038 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0329 (7)	0.0327 (7)	0.0482 (8)	−0.0051 (6)	0.0196 (6)	−0.0060 (6)
O2	0.0358 (6)	0.0331 (6)	0.0491 (7)	−0.0077 (5)	0.0195 (5)	−0.0075 (5)
C3	0.0317 (7)	0.0340 (8)	0.0272 (7)	−0.0010 (6)	0.0088 (6)	−0.0008 (6)
C4	0.0295 (8)	0.0505 (10)	0.0307 (8)	−0.0054 (7)	0.0097 (6)	−0.0004 (7)
C5	0.0285 (8)	0.0572 (11)	0.0292 (8)	0.0099 (7)	0.0099 (6)	0.0013 (7)
F5	0.0345 (5)	0.0779 (8)	0.0488 (6)	0.0126 (5)	0.0192 (5)	−0.0025 (6)
C6	0.0384 (9)	0.0414 (9)	0.0357 (9)	0.0107 (7)	0.0095 (7)	−0.0044 (7)
C7	0.0320 (8)	0.0322 (8)	0.0309 (8)	0.0023 (6)	0.0065 (6)	−0.0020 (6)
C8	0.0254 (7)	0.0307 (8)	0.0239 (7)	0.0011 (6)	0.0056 (5)	0.0012 (6)
C9	0.0293 (7)	0.0268 (7)	0.0271 (7)	0.0003 (6)	0.0088 (6)	−0.0008 (6)
C10	0.0270 (7)	0.0216 (7)	0.0292 (7)	0.0005 (5)	0.0093 (6)	−0.0007 (6)
C11	0.0304 (7)	0.0250 (7)	0.0228 (7)	0.0008 (6)	0.0096 (6)	−0.0014 (5)
C12	0.0302 (7)	0.0247 (7)	0.0208 (7)	0.0009 (6)	0.0078 (5)	−0.0030 (5)
N13	0.0262 (6)	0.0167 (6)	0.0208 (6)	0.0007 (4)	0.0068 (4)	−0.0008 (4)
C14	0.0273 (7)	0.0230 (7)	0.0211 (6)	0.0004 (5)	0.0054 (5)	0.0020 (5)
C15	0.0264 (7)	0.0262 (7)	0.0233 (7)	−0.0007 (6)	0.0049 (5)	0.0003 (6)
C16	0.0247 (6)	0.0210 (7)	0.0259 (7)	−0.0008 (5)	0.0071 (5)	−0.0025 (5)
C17	0.0279 (7)	0.0215 (7)	0.0262 (7)	0.0010 (5)	0.0086 (6)	−0.0015 (5)
C18	0.0293 (7)	0.0240 (7)	0.0311 (7)	−0.0004 (6)	0.0105 (6)	−0.0026 (6)
C19	0.0308 (7)	0.0239 (7)	0.0316 (8)	0.0025 (6)	0.0122 (6)	0.0048 (6)
N20	0.0317 (6)	0.0263 (6)	0.0240 (6)	0.0022 (5)	0.0105 (5)	0.0005 (5)
S21	0.03308 (18)	0.02227 (17)	0.02370 (17)	0.00310 (13)	0.01046 (14)	0.00323 (13)
O21B	0.0422 (6)	0.0338 (6)	0.0236 (5)	0.0053 (5)	0.0122 (4)	0.0045 (4)
O21A	0.0424 (6)	0.0219 (5)	0.0365 (6)	0.0028 (4)	0.0163 (5)	0.0029 (4)
Cl1	0.0503 (2)	0.01765 (16)	0.02553 (18)	0.00297 (14)	0.00438 (15)	−0.00174 (12)
C22	0.0298 (8)	0.0204 (9)	0.0232 (10)	0.0030 (7)	0.0070 (6)	−0.0016 (7)
S23	0.0389 (3)	0.0251 (2)	0.0277 (3)	0.00047 (18)	0.0097 (2)	−0.00483 (18)
C24	0.0314 (9)	0.0267 (9)	0.0232 (10)	0.0007 (7)	0.0012 (6)	0.0021 (7)
C25	0.0410 (9)	0.0284 (9)	0.0282 (8)	−0.0059 (8)	−0.0004 (7)	−0.0002 (7)
C26	0.0365 (11)	0.0363 (11)	0.0273 (13)	−0.0142 (8)	−0.0021 (11)	0.0035 (8)
Cl26	0.0664 (3)	0.0541 (3)	0.0488 (3)	−0.0342 (3)	0.0080 (2)	0.0020 (2)
C27	0.0338 (9)	0.0456 (11)	0.0328 (9)	−0.0083 (8)	0.0067 (7)	0.0037 (8)
C28	0.0367 (9)	0.0367 (10)	0.0332 (9)	−0.0049 (7)	0.0117 (7)	−0.0050 (8)
C29	0.0303 (8)	0.0273 (9)	0.0257 (9)	0.0000 (7)	0.0052 (7)	−0.0006 (7)
C30	0.0319 (8)	0.0216 (8)	0.0289 (8)	0.0041 (6)	0.0067 (6)	−0.0034 (6)
C22A	0.0298 (8)	0.0204 (9)	0.0232 (10)	0.0030 (7)	0.0070 (6)	−0.0016 (7)
S23A	0.0664 (3)	0.0541 (3)	0.0488 (3)	−0.0342 (3)	0.0080 (2)	0.0020 (2)
C24A	0.0314 (9)	0.0267 (9)	0.0232 (10)	0.0007 (7)	0.0012 (6)	0.0021 (7)
C25A	0.0410 (9)	0.0284 (9)	0.0282 (8)	−0.0059 (8)	−0.0004 (7)	−0.0002 (7)
C26A	0.0365 (11)	0.0363 (11)	0.0273 (13)	−0.0142 (8)	−0.0021 (11)	0.0035 (8)
Cl2A	0.047 (4)	0.051 (5)	0.047 (5)	−0.005 (4)	0.022 (4)	−0.010 (4)
C27A	0.0338 (9)	0.0456 (11)	0.0328 (9)	−0.0083 (8)	0.0067 (7)	0.0037 (8)
C28A	0.0367 (9)	0.0367 (10)	0.0332 (9)	−0.0049 (7)	0.0117 (7)	−0.0050 (8)
C29A	0.0303 (8)	0.0273 (9)	0.0257 (9)	0.0000 (7)	0.0052 (7)	−0.0006 (7)
C30A	0.0319 (8)	0.0216 (8)	0.0289 (8)	0.0041 (6)	0.0067 (6)	−0.0034 (6)

Geometric parameters (Å, º)

N1—C9	1.302 (2)	C18—H18B	0.99
N1—O2	1.4359 (16)	C19—N20	1.4769 (19)
O2—C3	1.3566 (19)	C19—H19A	0.99
C3—C8	1.384 (2)	C19—H19B	0.99
C3—C4	1.389 (2)	N20—S21	1.6166 (12)
C4—C5	1.368 (3)	N20—H20	0.852 (19)
C4—H4	0.95	S21—O21A	1.4329 (11)
C5—F5	1.3607 (18)	S21—O21B	1.4349 (11)
C5—C6	1.390 (3)	S21—C22A	1.75 (3)
C6—C7	1.383 (2)	S21—C22	1.7574 (19)
C6—H6	0.95	C22—C30	1.391 (5)
C7—C8	1.402 (2)	C22—S23	1.7418 (16)
C7—H7	0.95	S23—C24	1.7368 (19)
C8—C9	1.434 (2)	C24—C25	1.399 (2)
C9—C10	1.499 (2)	C24—C29	1.410 (2)
C10—C15	1.5293 (19)	C25—C26	1.380 (3)
C10—C11	1.5323 (19)	C25—H25	0.95
C10—H10	1	C26—C27	1.397 (3)
C11—C12	1.517 (2)	C26—Cl26	1.738 (2)
C11—H11A	0.99	C27—C28	1.378 (3)
C11—H11B	0.99	C27—H27	0.95
C12—N13	1.5013 (17)	C28—C29	1.408 (2)
C12—H12A	0.99	C28—H28	0.95
C12—H12B	0.99	C29—C30	1.407 (4)
N13—C16	1.4972 (17)	C30—H30	0.95
N13—C14	1.5008 (17)	C22A—C30A	1.399 (10)
N13—H13	0.911 (18)	C22A—S23A	1.716 (10)
C14—C15	1.5184 (19)	S23A—C24A	1.737 (10)
C14—H14A	0.99	C24A—C29A	1.400 (10)
C14—H14B	0.99	C24A—C25A	1.410 (10)
C15—H15A	0.99	C25A—C26A	1.399 (10)
C15—H15B	0.99	C25A—H25A	0.95
C16—C17	1.5173 (19)	C26A—C27A	1.402 (10)
C16—H16A	0.99	C26A—Cl2A	1.81 (5)
C16—H16B	0.99	C27A—C28A	1.400 (10)
C17—C18	1.5300 (19)	C27A—H27A	0.95
C17—H17A	0.99	C28A—C29A	1.404 (10)
C17—H17B	0.99	C28A—H28A	0.95
C18—C19	1.516 (2)	C29A—C30A	1.398 (10)
C18—H18A	0.99	C30A—H30A	0.95
C9—N1—O2	106.90 (12)	C17—C18—H18A	108.5
C3—O2—N1	107.22 (11)	C19—C18—H18B	108.5
O2—C3—C8	110.42 (13)	C17—C18—H18B	108.5
O2—C3—C4	126.17 (15)	H18A—C18—H18B	107.5
C8—C3—C4	123.39 (15)	N20—C19—C18	114.34 (12)
C5—C4—C3	114.09 (15)	N20—C19—H19A	108.7
C5—C4—H4	123	C18—C19—H19A	108.7
C3—C4—H4	123	N20—C19—H19B	108.7
F5—C5—C4	117.06 (16)	C18—C19—H19B	108.7
F5—C5—C6	117.55 (16)	H19A—C19—H19B	107.6
C4—C5—C6	125.39 (15)	C19—N20—S21	119.81 (10)
C7—C6—C5	119.15 (16)	C19—N20—H20	113.1 (13)
C7—C6—H6	120.4	S21—N20—H20	110.2 (13)
C5—C6—H6	120.4	O21A—S21—O21B	120.65 (6)
C6—C7—C8	117.66 (15)	O21A—S21—N20	106.37 (7)
C6—C7—H7	121.2	O21B—S21—N20	107.50 (7)
C8—C7—H7	121.2	O21A—S21—C22A	118.5 (11)
C3—C8—C7	120.32 (14)	O21B—S21—C22A	96.7 (13)
C3—C8—C9	103.70 (13)	N20—S21—C22A	105.9 (18)
C7—C8—C9	135.90 (14)	O21A—S21—C22	106.57 (7)
N1—C9—C8	111.74 (13)	O21B—S21—C22	106.56 (8)
N1—C9—C10	120.91 (13)	N20—S21—C22	108.80 (9)
C8—C9—C10	127.34 (13)	C30—C22—S23	113.54 (18)
C9—C10—C15	112.59 (12)	C30—C22—S21	126.52 (19)
C9—C10—C11	110.98 (12)	S23—C22—S21	119.90 (9)
C15—C10—C11	108.11 (11)	C24—S23—C22	90.32 (8)
C9—C10—H10	108.4	C25—C24—C29	121.79 (17)
C15—C10—H10	108.4	C25—C24—S23	126.55 (14)
C11—C10—H10	108.4	C29—C24—S23	111.65 (13)
C12—C11—C10	109.75 (12)	C26—C25—C24	116.76 (17)
C12—C11—H11A	109.7	C26—C25—H25	121.6
C10—C11—H11A	109.7	C24—C25—H25	121.6
C12—C11—H11B	109.7	C25—C26—C27	122.87 (18)
C10—C11—H11B	109.7	C25—C26—Cl26	119.42 (16)
H11A—C11—H11B	108.2	C27—C26—Cl26	117.71 (18)
N13—C12—C11	110.92 (11)	C28—C27—C26	120.09 (19)
N13—C12—H12A	109.5	C28—C27—H27	120
C11—C12—H12A	109.5	C26—C27—H27	120
N13—C12—H12B	109.5	C27—C28—C29	119.13 (17)
C11—C12—H12B	109.5	C27—C28—H28	120.4
H12A—C12—H12B	108	C29—C28—H28	120.4
C16—N13—C14	112.71 (11)	C30—C29—C28	127.3 (2)
C16—N13—C12	109.50 (10)	C30—C29—C24	113.3 (2)
C14—N13—C12	111.04 (10)	C28—C29—C24	119.35 (16)
C16—N13—H13	109.0 (10)	C22—C30—C29	111.1 (3)
C14—N13—H13	105.5 (10)	C22—C30—H30	124.4
C12—N13—H13	108.9 (11)	C29—C30—H30	124.4
N13—C14—C15	110.99 (11)	C30A—C22A—S23A	112 (2)
N13—C14—H14A	109.4	C30A—C22A—S21	139 (2)
C15—C14—H14A	109.4	S23A—C22A—S21	108.0 (16)
N13—C14—H14B	109.4	C22A—S23A—C24A	92.8 (18)
C15—C14—H14B	109.4	C29A—C24A—C25A	124.9 (16)
H14A—C14—H14B	108	C29A—C24A—S23A	108 (2)
C14—C15—C10	111.32 (11)	C25A—C24A—S23A	127 (2)
C14—C15—H15A	109.4	C26A—C25A—C24A	110 (3)
C10—C15—H15A	109.4	C26A—C25A—H25A	124.9
C14—C15—H15B	109.4	C24A—C25A—H25A	124.9
C10—C15—H15B	109.4	C25A—C26A—C27A	125 (4)
H15A—C15—H15B	108	C25A—C26A—Cl2A	123 (3)
N13—C16—C17	115.71 (11)	C27A—C26A—Cl2A	108 (3)
N13—C16—H16A	108.4	C28A—C27A—C26A	122 (4)
C17—C16—H16A	108.4	C28A—C27A—H27A	118.8
N13—C16—H16B	108.4	C26A—C27A—H27A	118.8
C17—C16—H16B	108.4	C27A—C28A—C29A	113 (3)
H16A—C16—H16B	107.4	C27A—C28A—H28A	123.5
C16—C17—C18	106.94 (11)	C29A—C28A—H28A	123.5
C16—C17—H17A	110.3	C30A—C29A—C24A	116 (2)
C18—C17—H17A	110.3	C30A—C29A—C28A	120 (2)
C16—C17—H17B	110.3	C24A—C29A—C28A	123 (2)
C18—C17—H17B	110.3	C29A—C30A—C22A	109.3 (16)
H17A—C17—H17B	108.6	C29A—C30A—H30A	125.4
C19—C18—C17	115.29 (12)	C22A—C30A—H30A	125.4
C19—C18—H18A	108.5
C9—N1—O2—C3	0.78 (17)	O21B—S21—C22—S23	−28.77 (17)
N1—O2—C3—C8	−1.07 (17)	N20—S21—C22—S23	86.86 (15)
N1—O2—C3—C4	177.20 (15)	C30—C22—S23—C24	1.3 (3)
O2—C3—C4—C5	−178.53 (15)	S21—C22—S23—C24	−176.65 (15)
C8—C3—C4—C5	−0.5 (2)	C22—S23—C24—C25	178.13 (18)
C3—C4—C5—F5	−179.29 (13)	C22—S23—C24—C29	−1.33 (16)
C3—C4—C5—C6	0.7 (2)	C29—C24—C25—C26	−1.0 (3)
F5—C5—C6—C7	179.66 (14)	S23—C24—C25—C26	179.63 (17)
C4—C5—C6—C7	−0.4 (3)	C24—C25—C26—C27	0.9 (3)
C5—C6—C7—C8	−0.3 (2)	C24—C25—C26—Cl26	180.00 (16)
O2—C3—C8—C7	178.19 (13)	C25—C26—C27—C28	−0.6 (3)
C4—C3—C8—C7	−0.1 (2)	Cl26—C26—C27—C28	−179.78 (16)
O2—C3—C8—C9	0.92 (16)	C26—C27—C28—C29	0.4 (3)
C4—C3—C8—C9	−177.41 (14)	C27—C28—C29—C30	178.6 (3)
C6—C7—C8—C3	0.5 (2)	C27—C28—C29—C24	−0.5 (3)
C6—C7—C8—C9	176.72 (16)	C25—C24—C29—C30	−178.4 (3)
O2—N1—C9—C8	−0.21 (17)	S23—C24—C29—C30	1.1 (3)
O2—N1—C9—C10	178.94 (12)	C25—C24—C29—C28	0.8 (3)
C3—C8—C9—N1	−0.42 (17)	S23—C24—C29—C28	−179.72 (14)
C7—C8—C9—N1	−177.03 (17)	S23—C22—C30—C29	−0.9 (4)
C3—C8—C9—C10	−179.50 (14)	S21—C22—C30—C29	176.9 (2)
C7—C8—C9—C10	3.9 (3)	C28—C29—C30—C22	−179.2 (2)
N1—C9—C10—C15	43.90 (19)	C24—C29—C30—C22	−0.1 (5)
C8—C9—C10—C15	−137.10 (15)	O21A—S21—C22A—C30A	−172 (6)
N1—C9—C10—C11	−77.43 (17)	O21B—S21—C22A—C30A	−41 (7)
C8—C9—C10—C11	101.57 (17)	N20—S21—C22A—C30A	69 (7)
C9—C10—C11—C12	−176.77 (12)	O21A—S21—C22A—S23A	22 (4)
C15—C10—C11—C12	59.30 (15)	O21B—S21—C22A—S23A	152 (3)
C10—C11—C12—N13	−59.77 (15)	N20—S21—C22A—S23A	−98 (3)
C11—C12—N13—C16	−177.63 (11)	C30A—C22A—S23A—C24A	9 (5)
C11—C12—N13—C14	57.27 (15)	S21—C22A—S23A—C24A	179 (3)
C16—N13—C14—C15	−178.50 (11)	C22A—S23A—C24A—C29A	0 (4)
C12—N13—C14—C15	−55.22 (15)	C22A—S23A—C24A—C25A	178 (4)
N13—C14—C15—C10	56.61 (15)	C29A—C24A—C25A—C26A	−10 (6)
C9—C10—C15—C14	178.89 (12)	S23A—C24A—C25A—C26A	173 (4)
C11—C10—C15—C14	−58.15 (15)	C24A—C25A—C26A—C27A	16 (7)
C14—N13—C16—C17	−68.02 (15)	C24A—C25A—C26A—Cl2A	171 (4)
C12—N13—C16—C17	167.84 (11)	C25A—C26A—C27A—C28A	−17 (8)
N13—C16—C17—C18	176.40 (11)	Cl2A—C26A—C27A—C28A	−174 (3)
C16—C17—C18—C19	−174.57 (12)	C26A—C27A—C28A—C29A	8 (6)
C17—C18—C19—N20	−63.70 (17)	C25A—C24A—C29A—C30A	173 (4)
C18—C19—N20—S21	−83.56 (14)	S23A—C24A—C29A—C30A	−10 (5)
C19—N20—S21—O21A	−176.15 (10)	C25A—C24A—C29A—C28A	4 (7)
C19—N20—S21—O21B	53.33 (12)	S23A—C24A—C29A—C28A	−178 (3)
C19—N20—S21—C22A	−49.2 (11)	C27A—C28A—C29A—C30A	−171 (4)
C19—N20—S21—C22	−61.70 (12)	C27A—C28A—C29A—C24A	−2 (6)
O21A—S21—C22—C30	23.5 (3)	C24A—C29A—C30A—C22A	16 (6)
O21B—S21—C22—C30	153.6 (3)	C28A—C29A—C30A—C22A	−175 (4)
N20—S21—C22—C30	−90.8 (3)	S23A—C22A—C30A—C29A	−15 (6)
O21A—S21—C22—S23	−158.81 (13)	S21—C22A—C30A—C29A	179 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13···Cl1	0.911 (18)	2.130 (19)	3.0391 (12)	175.3 (15)
N20—H20···Cl1^i	0.852 (19)	2.39 (2)	3.1700 (13)	152.8 (17)
C4—H4···Cl26^ii	0.95	2.77	3.5576 (18)	141
C14—H14B···Cl1^iii	0.99	2.84	3.7256 (15)	150
C16—H16A···Cl1^iv	0.99	2.66	3.6297 (14)	166
C16—H16B···Cl1^iii	0.99	2.66	3.6011 (14)	159
C4—H4···F5^v	0.95	2.49	3.083 (2)	121
C11—H11A···O21A^iv	0.99	2.6	3.5784 (17)	171
C18—H18B···O21B	0.99	2.49	3.1627 (18)	125
C19—H19B···S23	0.99	2.85	3.6740 (16)	141

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

4-(6-Fluoro-1,2-benzoxazol-3-yl)-1-[3-(3-chloro-4-fluorobenzenesulfonamido)propyl]piperidin-1-ium chloride (IV)

Crystal data

C21H23ClF2N3O3S^+·Cl^−	F(000) = 1048
Mr = 506.38	Dx = 1.462 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6532 reflections
a = 5.7077 (2) Å	θ = 4.3–76.2°
b = 9.7798 (3) Å	µ = 0.42 mm^−1
c = 41.2280 (11) Å	T = 123 K
β = 91.123 (2)°	Plate, white
V = 2300.91 (12) Å^3	0.2 × 0.2 × 0.03 mm
Z = 4

Data collection

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	4817 independent reflections
Mirror monochromator	3625 reflections with I > 2σ(I)
Detector resolution: 10.3756 pixels mm^-1	Rint = 0.097
ω scans	θmax = 26.7°, θmin = 2.0°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −7→7
Tmin = 0.521, Tmax = 1	k = −12→12
34975 measured reflections	l = −51→51

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.100	w = 1/[σ^2(Fo^2) + (0.0355P)^2 + 1.0922P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
4817 reflections	Δρmax = 0.28 e Å^−3
297 parameters	Δρmin = −0.38 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
N1	0.5656 (4)	0.3027 (2)	0.10024 (5)	0.0331 (5)
O2	0.5563 (4)	0.3341 (2)	0.06626 (4)	0.0350 (5)
C3	0.3670 (5)	0.2681 (3)	0.05338 (6)	0.0283 (6)
C4	0.2955 (5)	0.2705 (3)	0.02076 (6)	0.0343 (6)
H4	0.3768	0.319	0.0045	0.041*
C5	0.0967 (6)	0.1959 (3)	0.01457 (6)	0.0368 (7)
F5	0.0133 (3)	0.19257 (19)	−0.01662 (4)	0.0484 (5)
C6	−0.0290 (5)	0.1233 (3)	0.03747 (7)	0.0376 (7)
H6	−0.1668	0.0749	0.0312	0.045*
C7	0.0484 (5)	0.1224 (3)	0.06928 (6)	0.0312 (6)
H7	−0.033	0.073	0.0854	0.037*
C8	0.2508 (5)	0.1967 (2)	0.07707 (6)	0.0262 (5)
C9	0.3883 (5)	0.2233 (2)	0.10601 (6)	0.0247 (5)
C10	0.3434 (4)	0.1703 (2)	0.13947 (6)	0.0232 (5)
H10	0.2394	0.0885	0.1372	0.028*
C11	0.5677 (5)	0.1251 (3)	0.15706 (6)	0.0263 (5)
H11A	0.6486	0.0557	0.1439	0.032*
H11B	0.6738	0.2045	0.1598	0.032*
C12	0.5130 (4)	0.0652 (2)	0.19011 (6)	0.0227 (5)
H12A	0.4164	−0.0181	0.1873	0.027*
H12B	0.6609	0.039	0.2014	0.027*
N13	0.3840 (3)	0.16694 (19)	0.21031 (5)	0.0184 (4)
C14	0.1641 (4)	0.2147 (2)	0.19346 (6)	0.0226 (5)
H14A	0.0869	0.2845	0.207	0.027*
H14B	0.055	0.1367	0.1907	0.027*
C15	0.2167 (4)	0.2753 (2)	0.16037 (6)	0.0236 (5)
H15A	0.316	0.3577	0.1632	0.028*
H15B	0.0685	0.3032	0.1494	0.028*
C16	0.3381 (4)	0.1076 (2)	0.24301 (5)	0.0216 (5)
H16A	0.4861	0.0689	0.2519	0.026*
H16B	0.225	0.0315	0.2404	0.026*
C17	0.2424 (4)	0.2089 (2)	0.26732 (5)	0.0220 (5)
H17A	0.0737	0.225	0.2627	0.026*
H17B	0.3257	0.2973	0.2655	0.026*
C18	0.2758 (4)	0.1519 (3)	0.30158 (6)	0.0230 (5)
H18A	0.175	0.2034	0.3166	0.028*
H18B	0.2254	0.0551	0.3018	0.028*
N20	0.5197 (4)	0.1608 (2)	0.31309 (5)	0.0243 (5)
S21	0.59319 (10)	0.26565 (6)	0.34115 (2)	0.02039 (13)
O21A	0.4841 (3)	0.39563 (17)	0.33432 (4)	0.0264 (4)
O21B	0.8427 (3)	0.25907 (19)	0.34505 (4)	0.0297 (4)
C22	0.4690 (4)	0.2073 (2)	0.37773 (6)	0.0219 (5)
C23	0.5643 (5)	0.0930 (3)	0.39350 (6)	0.0286 (6)
H23	0.6912	0.0445	0.3844	0.034*
C24	0.4704 (5)	0.0515 (3)	0.42278 (6)	0.0336 (6)
H24	0.5322	−0.0259	0.4339	0.04*
C25	0.2875 (5)	0.1239 (3)	0.43533 (6)	0.0309 (6)
F25	0.1986 (3)	0.08435 (17)	0.46410 (4)	0.0427 (4)
C26	0.1919 (5)	0.2368 (3)	0.41981 (6)	0.0273 (5)
Cl26	−0.03838 (13)	0.32463 (8)	0.43676 (2)	0.03877 (18)
C27	0.2830 (4)	0.2782 (2)	0.39056 (6)	0.0238 (5)
H27	0.2183	0.3548	0.3794	0.029*
Cl1	0.68751 (10)	0.41961 (6)	0.22042 (2)	0.02532 (14)
H13	0.481 (5)	0.248 (3)	0.2128 (6)	0.025 (7)*
H20	0.618 (6)	0.098 (4)	0.3095 (8)	0.057 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0398 (14)	0.0359 (12)	0.0239 (11)	−0.0073 (11)	0.0050 (10)	0.0029 (9)
O2	0.0421 (12)	0.0395 (11)	0.0236 (9)	−0.0124 (9)	0.0068 (8)	0.0049 (8)
C3	0.0340 (15)	0.0266 (12)	0.0247 (12)	0.0008 (11)	0.0075 (11)	0.0003 (10)
C4	0.0482 (19)	0.0330 (14)	0.0221 (12)	0.0061 (13)	0.0079 (12)	0.0000 (11)
C5	0.051 (2)	0.0362 (15)	0.0225 (13)	0.0098 (13)	−0.0037 (12)	−0.0027 (11)
F5	0.0646 (13)	0.0560 (11)	0.0241 (8)	0.0072 (10)	−0.0096 (8)	−0.0022 (8)
C6	0.0391 (18)	0.0404 (16)	0.0332 (15)	−0.0001 (13)	−0.0048 (13)	−0.0021 (12)
C7	0.0305 (16)	0.0331 (14)	0.0301 (14)	−0.0012 (12)	0.0021 (11)	0.0014 (11)
C8	0.0314 (15)	0.0230 (12)	0.0242 (12)	0.0039 (10)	0.0035 (11)	−0.0017 (9)
C9	0.0272 (14)	0.0229 (12)	0.0242 (12)	0.0021 (10)	0.0036 (10)	−0.0018 (9)
C10	0.0235 (14)	0.0222 (11)	0.0241 (12)	−0.0020 (10)	0.0022 (10)	0.0010 (9)
C11	0.0253 (14)	0.0278 (12)	0.0260 (12)	0.0045 (10)	0.0054 (10)	0.0024 (10)
C12	0.0212 (13)	0.0201 (11)	0.0270 (12)	0.0053 (9)	0.0025 (10)	0.0007 (9)
N13	0.0162 (10)	0.0163 (9)	0.0227 (10)	0.0008 (8)	0.0012 (8)	−0.0002 (7)
C14	0.0159 (12)	0.0248 (12)	0.0271 (12)	0.0036 (9)	0.0006 (10)	0.0007 (9)
C15	0.0197 (13)	0.0259 (12)	0.0250 (12)	0.0020 (10)	−0.0004 (10)	0.0028 (9)
C16	0.0251 (13)	0.0184 (11)	0.0215 (11)	0.0007 (9)	0.0010 (10)	0.0015 (9)
C17	0.0212 (13)	0.0210 (11)	0.0236 (11)	0.0021 (9)	0.0011 (10)	−0.0021 (9)
C18	0.0178 (13)	0.0275 (12)	0.0237 (12)	−0.0030 (10)	0.0022 (10)	−0.0023 (9)
N20	0.0188 (11)	0.0289 (11)	0.0252 (10)	0.0058 (9)	−0.0004 (9)	−0.0071 (9)
S21	0.0160 (3)	0.0222 (3)	0.0230 (3)	0.0005 (2)	0.0028 (2)	−0.0020 (2)
O21A	0.0250 (10)	0.0230 (9)	0.0315 (9)	−0.0006 (7)	0.0061 (8)	0.0008 (7)
O21B	0.0165 (9)	0.0415 (11)	0.0311 (9)	0.0003 (8)	0.0028 (7)	−0.0042 (8)
C22	0.0199 (13)	0.0242 (12)	0.0218 (11)	−0.0015 (9)	−0.0008 (9)	−0.0029 (9)
C23	0.0269 (15)	0.0255 (12)	0.0334 (14)	0.0027 (11)	0.0015 (11)	−0.0015 (10)
C24	0.0424 (18)	0.0266 (13)	0.0319 (14)	0.0025 (12)	−0.0001 (12)	0.0057 (10)
C25	0.0397 (17)	0.0306 (13)	0.0227 (12)	−0.0102 (12)	0.0039 (11)	0.0011 (10)
F25	0.0608 (12)	0.0391 (9)	0.0287 (8)	−0.0068 (8)	0.0131 (8)	0.0072 (7)
C26	0.0248 (14)	0.0307 (13)	0.0267 (12)	−0.0017 (11)	0.0050 (10)	−0.0066 (10)
Cl26	0.0362 (4)	0.0467 (4)	0.0340 (3)	0.0057 (3)	0.0153 (3)	−0.0046 (3)
C27	0.0226 (13)	0.0248 (12)	0.0239 (12)	−0.0007 (10)	−0.0024 (10)	−0.0009 (9)
Cl1	0.0181 (3)	0.0199 (3)	0.0380 (3)	−0.0033 (2)	0.0009 (2)	0.0006 (2)

Geometric parameters (Å, º)

N1—C9	1.301 (3)	C14—H14B	0.99
N1—O2	1.434 (3)	C15—H15A	0.99
O2—C3	1.358 (3)	C15—H15B	0.99
C3—C8	1.381 (3)	C16—C17	1.519 (3)
C3—C4	1.398 (4)	C16—H16A	0.99
C4—C5	1.369 (4)	C16—H16B	0.99
C4—H4	0.95	C17—C18	1.527 (3)
C5—F5	1.363 (3)	C17—H17A	0.99
C5—C6	1.392 (4)	C17—H17B	0.99
C6—C7	1.376 (4)	C18—N20	1.464 (3)
C6—H6	0.95	C18—H18A	0.99
C7—C8	1.397 (4)	C18—H18B	0.99
C7—H7	0.95	N20—S21	1.596 (2)
C8—C9	1.439 (3)	N20—H20	0.85 (3)
C9—C10	1.500 (3)	S21—O21B	1.4318 (18)
C10—C11	1.525 (3)	S21—O21A	1.4407 (17)
C10—C15	1.531 (3)	S21—C22	1.774 (2)
C10—H10	1	C22—C27	1.382 (3)
C11—C12	1.521 (3)	C22—C23	1.398 (3)
C11—H11A	0.99	C23—C24	1.391 (4)
C11—H11B	0.99	C23—H23	0.95
C12—N13	1.500 (3)	C24—C25	1.371 (4)
C12—H12A	0.99	C24—H24	0.95
C12—H12B	0.99	C25—F25	1.356 (3)
N13—C16	1.495 (3)	C25—C26	1.382 (4)
N13—C14	1.497 (3)	C26—C27	1.383 (3)
N13—H13	0.97 (3)	C26—Cl26	1.729 (3)
C14—C15	1.523 (3)	C27—H27	0.95
C14—H14A	0.99
C9—N1—O2	107.0 (2)	H14A—C14—H14B	108
C3—O2—N1	107.15 (18)	C14—C15—C10	110.27 (19)
O2—C3—C8	110.7 (2)	C14—C15—H15A	109.6
O2—C3—C4	125.7 (2)	C10—C15—H15A	109.6
C8—C3—C4	123.6 (3)	C14—C15—H15B	109.6
C5—C4—C3	113.3 (3)	C10—C15—H15B	109.6
C5—C4—H4	123.3	H15A—C15—H15B	108.1
C3—C4—H4	123.3	N13—C16—C17	114.42 (18)
F5—C5—C4	117.5 (3)	N13—C16—H16A	108.7
F5—C5—C6	116.9 (3)	C17—C16—H16A	108.7
C4—C5—C6	125.6 (3)	N13—C16—H16B	108.7
C7—C6—C5	119.3 (3)	C17—C16—H16B	108.7
C7—C6—H6	120.3	H16A—C16—H16B	107.6
C5—C6—H6	120.3	C16—C17—C18	109.42 (19)
C6—C7—C8	117.7 (3)	C16—C17—H17A	109.8
C6—C7—H7	121.2	C18—C17—H17A	109.8
C8—C7—H7	121.2	C16—C17—H17B	109.8
C3—C8—C7	120.5 (2)	C18—C17—H17B	109.8
C3—C8—C9	103.5 (2)	H17A—C17—H17B	108.2
C7—C8—C9	136.1 (2)	N20—C18—C17	112.3 (2)
N1—C9—C8	111.7 (2)	N20—C18—H18A	109.2
N1—C9—C10	121.5 (2)	C17—C18—H18A	109.2
C8—C9—C10	126.8 (2)	N20—C18—H18B	109.2
C9—C10—C11	112.4 (2)	C17—C18—H18B	109.2
C9—C10—C15	112.1 (2)	H18A—C18—H18B	107.9
C11—C10—C15	109.15 (19)	C18—N20—S21	120.51 (17)
C9—C10—H10	107.7	C18—N20—H20	122 (2)
C11—C10—H10	107.7	S21—N20—H20	115 (2)
C15—C10—H10	107.7	O21B—S21—O21A	119.12 (11)
C12—C11—C10	110.7 (2)	O21B—S21—N20	107.42 (11)
C12—C11—H11A	109.5	O21A—S21—N20	108.59 (11)
C10—C11—H11A	109.5	O21B—S21—C22	107.66 (11)
C12—C11—H11B	109.5	O21A—S21—C22	105.76 (11)
C10—C11—H11B	109.5	N20—S21—C22	107.83 (11)
H11A—C11—H11B	108.1	C27—C22—C23	121.2 (2)
N13—C12—C11	110.70 (19)	C27—C22—S21	119.14 (19)
N13—C12—H12A	109.5	C23—C22—S21	119.64 (19)
C11—C12—H12A	109.5	C24—C23—C22	119.0 (2)
N13—C12—H12B	109.5	C24—C23—H23	120.5
C11—C12—H12B	109.5	C22—C23—H23	120.5
H12A—C12—H12B	108.1	C25—C24—C23	119.1 (2)
C16—N13—C14	112.29 (18)	C25—C24—H24	120.5
C16—N13—C12	109.86 (17)	C23—C24—H24	120.5
C14—N13—C12	111.44 (18)	F25—C25—C24	118.9 (2)
C16—N13—H13	109.4 (15)	F25—C25—C26	118.8 (2)
C14—N13—H13	105.2 (16)	C24—C25—C26	122.3 (2)
C12—N13—H13	108.5 (15)	C25—C26—C27	119.1 (2)
N13—C14—C15	111.04 (19)	C25—C26—Cl26	120.4 (2)
N13—C14—H14A	109.4	C27—C26—Cl26	120.5 (2)
C15—C14—H14A	109.4	C22—C27—C26	119.4 (2)
N13—C14—H14B	109.4	C22—C27—H27	120.3
C15—C14—H14B	109.4	C26—C27—H27	120.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13···Cl1	0.97 (3)	2.07 (3)	3.042 (2)	177 (2)
N20—H20···Cl1^i	0.85 (3)	2.42 (4)	3.218 (2)	158 (3)
C14—H14A···Cl1^ii	0.99	2.7	3.574 (2)	147
C16—H16A···Cl1^i	0.99	2.61	3.581 (2)	167
C18—H18B···Cl1^iii	0.99	2.84	3.590 (2)	133
C10—H10···O21A^iii	1	2.57	3.458 (3)	148
C12—H12A···O21A^iii	0.99	2.58	3.421 (3)	143
C14—H14B···O21A^iii	0.99	2.58	3.424 (3)	143
C18—H18A···O21B^ii	0.99	2.31	3.255 (3)	158

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