2-{[2,8-Bis(trifluoro-meth-yl)quinolin-4-yl](hy-droxy)meth-yl}piperidin-1-ium 3-amino-5-nitro-benzoate sesquihydrate.

The asymmetric unit of the title salt solvate, C(17)H(17)F(6)N(2)O(+)·C(7)H(5)N(2)O(4) (-)·1.5H(2)O, comprises a piperidin-1-ium cation, a 3-amino-5-nitro-benzoate anion, and three fractionally occupied [i.e. 0.414 (3), 0.627 (6) and 0.459 (5)] disordered water mol-ecules of solvation. The cation has an L shape with a C-C-C-C torsion angle of -102.9 (3)° for the atoms linking the quinolinyl group to the rest of the cation. In the anion, the carboxyl-ate and nitro groups are essentially coplanar with the benzene ring [O-C-C-C torsion angle = 179.7 (2)° and O-N-C-C torsion angle = -3.9 (3)°]. In the crystal, extensive O-H⋯O, O-H⋯F and N-H⋯·O hydrogen bonding leads to the formation of a layer in the ab plane.

Related literature

For background information on mefloquine and derivatives, see: Kunin & Ellis (2007 ▶); Maguire et al. (2006 ▶); Dow et al. (2004 ▶). For selected crystal structures of mefloquine and its salts, see: Obaleye et al. (2009 ▶); Skórska et al. (2005 ▶); Karle & Karle (1991 ▶, 2002 ▶); Wardell et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C17H17F6N2O+·C7H5N2O4 −·1.5H2O

M = 587.48

Triclinic,

a = 9.1705 (5) Å

b = 12.5446 (9) Å

c = 12.7788 (8) Å

α = 66.278 (4)°

β = 77.261 (4)°

γ = 71.537 (4)°

V = 1269.23 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.14 mm−1

T = 120 K

0.28 × 0.16 × 0.10 mm

Data collection

Bruker–Nonius APEXII CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.640, T max = 0.746

25681 measured reflections

5832 independent reflections

3477 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.174

S = 1.03

5832 reflections

416 parameters

15 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.38 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681104270X/lh5355sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104270X/lh5355Isup2.hkl

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

C17H17F6N2O+·C7H5N2O4−·1.5H2O	Z = 2
Mr = 587.48	F(000) = 606
Triclinic, P1	Dx = 1.537 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.1705 (5) Å	Cell parameters from 30639 reflections
b = 12.5446 (9) Å	θ = 2.9–27.5°
c = 12.7788 (8) Å	µ = 0.14 mm−1
α = 66.278 (4)°	T = 120 K
β = 77.261 (4)°	Block, orange
γ = 71.537 (4)°	0.28 × 0.16 × 0.10 mm
V = 1269.23 (14) Å3

Bruker–Nonius APEXII CCD camera on κ-goniostat diffractometer	5832 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3477 reflections with I > 2σ(I)
10cm confocal mirrors	Rint = 0.078
Detector resolution: 9.091 pixels mm-1	θmax = 27.6°, θmin = 3.0°
φ & ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −16→16
Tmin = 0.640, Tmax = 0.746	l = −16→16
25681 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.174	w = 1/[σ2(Fo2) + (0.0836P)2 + 0.2367P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
5832 reflections	Δρmax = 0.39 e Å−3
416 parameters	Δρmin = −0.38 e Å−3
15 restraints	Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (4)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	Occ. (<1)
F1	0.87381 (17)	0.49471 (18)	0.83650 (15)	0.0532 (5)
F2	0.74544 (19)	0.50218 (18)	0.99348 (14)	0.0515 (5)
F3	0.7703 (2)	0.66464 (17)	0.8535 (2)	0.0766 (7)
F4	0.55227 (19)	0.21925 (14)	0.99220 (14)	0.0443 (4)
F5	0.69944 (17)	0.22502 (14)	0.83406 (15)	0.0457 (5)
F6	0.51655 (18)	0.13558 (14)	0.88618 (15)	0.0443 (4)
O1	0.3030 (2)	0.89697 (16)	0.68621 (16)	0.0321 (4)
H1	0.287 (4)	0.940 (2)	0.6179 (12)	0.048*
O2	0.2506 (2)	1.03009 (17)	0.46810 (18)	0.0442 (5)
O3	0.0666 (2)	1.19038 (17)	0.39087 (19)	0.0437 (5)
O4	0.0825 (2)	1.58565 (17)	0.37663 (17)	0.0409 (5)
O5	0.2815 (3)	1.60038 (18)	0.42819 (19)	0.0509 (6)
O1W	0.3447 (6)	1.0482 (5)	0.7901 (4)	0.0431 (14)	0.414 (3)
H1W1	0.358 (8)	0.991 (5)	0.768 (7)	0.065*	0.414 (3)
H1W2	0.413 (7)	1.086 (6)	0.754 (6)	0.065*	0.414 (3)
O2W	0.0428 (4)	1.1348 (3)	0.7158 (3)	0.0449 (11)	0.627 (6)
H2W1	0.128 (3)	1.133 (4)	0.733 (5)	0.067*	0.627 (6)
H2W2	−0.006 (5)	1.2078 (17)	0.689 (5)	0.067*	0.627 (6)
O3W	−0.0625 (6)	1.1518 (4)	0.6409 (4)	0.0467 (16)	0.459 (5)
H3W1	−0.022 (9)	1.158 (6)	0.573 (3)	0.070*	0.459 (5)
H3W2	−0.096 (9)	1.221 (3)	0.644 (6)	0.070*	0.459 (5)
N1	0.5885 (2)	0.46024 (19)	0.84811 (18)	0.0284 (5)
N2	−0.0203 (2)	0.9090 (2)	0.7489 (2)	0.0297 (5)
H21	−0.039 (3)	0.895 (3)	0.6913 (17)	0.036*
H22	0.008 (3)	0.9766 (16)	0.727 (2)	0.036*
N3	0.2069 (3)	1.5407 (2)	0.41647 (19)	0.0338 (5)
N4	0.6061 (3)	1.1835 (2)	0.5903 (2)	0.0467 (7)
H41	0.657 (3)	1.1130 (16)	0.585 (3)	0.056*
H42	0.660 (3)	1.230 (3)	0.590 (3)	0.056*
C1	0.6030 (3)	0.5648 (2)	0.8371 (2)	0.0273 (6)
C2	0.4964 (3)	0.6767 (2)	0.7926 (2)	0.0269 (6)
H2A	0.5132	0.7488	0.7899	0.032*
C3	0.3666 (3)	0.6788 (2)	0.7529 (2)	0.0261 (6)
C4	0.3486 (3)	0.5686 (2)	0.7576 (2)	0.0262 (6)
C5	0.2229 (3)	0.5601 (2)	0.7155 (2)	0.0295 (6)
H5	0.1475	0.6313	0.6800	0.035*
C6	0.2094 (3)	0.4515 (2)	0.7256 (2)	0.0320 (6)
H6A	0.1254	0.4478	0.6962	0.038*
C7	0.3189 (3)	0.3440 (2)	0.7793 (2)	0.0325 (6)
H7	0.3071	0.2686	0.7868	0.039*
C8	0.4418 (3)	0.3481 (2)	0.8204 (2)	0.0295 (6)
C9	0.4616 (3)	0.4604 (2)	0.8081 (2)	0.0273 (6)
C10	0.7471 (3)	0.5578 (2)	0.8802 (2)	0.0322 (6)
C11	0.5530 (3)	0.2330 (2)	0.8820 (3)	0.0350 (6)
C12	0.2441 (3)	0.7967 (2)	0.7111 (2)	0.0278 (6)
H12A	0.2092	0.8029	0.6396	0.033*
C13	0.1041 (3)	0.7996 (2)	0.8030 (2)	0.0281 (6)
H13	0.0664	0.7264	0.8232	0.034*
C14	−0.1666 (3)	0.9248 (3)	0.8275 (3)	0.0371 (7)
H14A	−0.2144	0.8581	0.8453	0.045*
H14B	−0.2404	1.0013	0.7885	0.045*
C15	−0.1351 (3)	0.9265 (3)	0.9384 (2)	0.0374 (7)
H15A	−0.2316	0.9299	0.9914	0.045*
H15B	−0.1005	0.9994	0.9217	0.045*
C16	−0.0107 (3)	0.8142 (3)	0.9959 (2)	0.0385 (7)
H16A	0.0126	0.8192	1.0656	0.046*
H16B	−0.0491	0.7416	1.0196	0.046*
C17	0.1353 (3)	0.8042 (3)	0.9131 (2)	0.0328 (6)
H17A	0.2141	0.7304	0.9506	0.039*
H17B	0.1773	0.8742	0.8939	0.039*
C18	0.1878 (3)	1.1404 (2)	0.4389 (2)	0.0297 (6)
C19	0.2628 (3)	1.2185 (2)	0.4629 (2)	0.0273 (6)
C20	0.1963 (3)	1.3416 (2)	0.4311 (2)	0.0275 (6)
H20	0.1021	1.3781	0.3969	0.033*
C21	0.2735 (3)	1.4088 (2)	0.4515 (2)	0.0294 (6)
C22	0.4084 (3)	1.3611 (2)	0.5017 (2)	0.0322 (6)
H22A	0.4565	1.4115	0.5137	0.039*
C23	0.4745 (3)	1.2369 (2)	0.5350 (2)	0.0325 (6)
C24	0.3990 (3)	1.1676 (2)	0.5141 (2)	0.0297 (6)
H24	0.4425	1.0832	0.5356	0.036*

	U11	U22	U33	U12	U13	U23
F1	0.0231 (8)	0.0818 (14)	0.0522 (11)	−0.0005 (8)	−0.0032 (7)	−0.0318 (10)
F2	0.0431 (10)	0.0790 (14)	0.0330 (9)	−0.0209 (9)	−0.0030 (7)	−0.0173 (9)
F3	0.0609 (12)	0.0301 (11)	0.140 (2)	−0.0128 (9)	−0.0556 (13)	−0.0075 (12)
F4	0.0490 (10)	0.0316 (10)	0.0437 (10)	−0.0045 (7)	−0.0151 (8)	−0.0043 (8)
F5	0.0274 (8)	0.0313 (9)	0.0670 (12)	0.0030 (7)	−0.0015 (8)	−0.0161 (9)
F6	0.0432 (9)	0.0209 (9)	0.0658 (11)	−0.0029 (7)	−0.0133 (8)	−0.0129 (8)
O1	0.0339 (10)	0.0219 (10)	0.0374 (10)	−0.0080 (8)	−0.0063 (8)	−0.0055 (8)
O2	0.0627 (13)	0.0206 (11)	0.0550 (13)	−0.0047 (9)	−0.0330 (11)	−0.0102 (9)
O3	0.0380 (11)	0.0283 (11)	0.0703 (14)	−0.0028 (9)	−0.0203 (10)	−0.0201 (11)
O4	0.0492 (12)	0.0263 (11)	0.0478 (12)	−0.0050 (9)	−0.0130 (10)	−0.0133 (10)
O5	0.0781 (15)	0.0252 (11)	0.0601 (14)	−0.0162 (10)	−0.0286 (12)	−0.0129 (10)
O1W	0.050 (3)	0.044 (3)	0.040 (3)	−0.017 (2)	−0.003 (2)	−0.019 (3)
O2W	0.043 (2)	0.032 (2)	0.056 (2)	−0.0070 (15)	−0.0043 (17)	−0.0147 (18)
O3W	0.049 (3)	0.030 (3)	0.055 (3)	−0.005 (2)	−0.003 (2)	−0.014 (2)
N1	0.0231 (11)	0.0252 (12)	0.0322 (12)	−0.0050 (9)	0.0003 (9)	−0.0081 (10)
N2	0.0301 (11)	0.0209 (12)	0.0385 (13)	−0.0007 (9)	−0.0104 (10)	−0.0120 (10)
N3	0.0525 (15)	0.0229 (12)	0.0296 (12)	−0.0110 (11)	−0.0067 (11)	−0.0107 (10)
N4	0.0625 (17)	0.0285 (14)	0.0600 (17)	−0.0056 (12)	−0.0316 (14)	−0.0185 (13)
C1	0.0240 (12)	0.0243 (14)	0.0288 (13)	−0.0051 (10)	−0.0005 (10)	−0.0066 (11)
C2	0.0273 (13)	0.0208 (13)	0.0288 (13)	−0.0066 (10)	0.0010 (10)	−0.0069 (11)
C3	0.0259 (13)	0.0218 (13)	0.0250 (12)	−0.0032 (10)	−0.0005 (10)	−0.0060 (11)
C4	0.0239 (12)	0.0234 (14)	0.0273 (13)	−0.0038 (10)	−0.0009 (10)	−0.0077 (11)
C5	0.0267 (13)	0.0240 (14)	0.0338 (14)	0.0004 (10)	−0.0028 (11)	−0.0119 (12)
C6	0.0265 (13)	0.0310 (15)	0.0389 (15)	−0.0043 (11)	−0.0037 (11)	−0.0152 (13)
C7	0.0300 (14)	0.0257 (15)	0.0416 (15)	−0.0041 (11)	−0.0019 (12)	−0.0153 (13)
C8	0.0256 (13)	0.0246 (14)	0.0354 (14)	−0.0014 (10)	−0.0016 (11)	−0.0125 (12)
C9	0.0207 (12)	0.0269 (14)	0.0299 (13)	−0.0044 (10)	0.0010 (10)	−0.0089 (11)
C10	0.0311 (14)	0.0240 (14)	0.0366 (15)	−0.0069 (11)	−0.0026 (12)	−0.0065 (12)
C11	0.0308 (14)	0.0220 (14)	0.0465 (17)	−0.0028 (11)	−0.0034 (12)	−0.0099 (13)
C12	0.0268 (13)	0.0188 (13)	0.0336 (14)	−0.0023 (10)	−0.0065 (11)	−0.0061 (11)
C13	0.0261 (13)	0.0150 (13)	0.0379 (14)	−0.0004 (10)	−0.0057 (11)	−0.0067 (11)
C14	0.0246 (13)	0.0301 (16)	0.0555 (18)	−0.0004 (11)	−0.0057 (12)	−0.0186 (14)
C15	0.0319 (14)	0.0318 (16)	0.0440 (16)	−0.0014 (12)	0.0000 (12)	−0.0162 (14)
C16	0.0350 (15)	0.0324 (16)	0.0402 (16)	−0.0012 (12)	0.0003 (12)	−0.0131 (14)
C17	0.0294 (13)	0.0281 (15)	0.0371 (15)	−0.0019 (11)	−0.0072 (11)	−0.0102 (12)
C18	0.0413 (15)	0.0230 (14)	0.0255 (13)	−0.0078 (12)	−0.0068 (11)	−0.0081 (11)
C19	0.0386 (14)	0.0244 (14)	0.0201 (12)	−0.0106 (11)	−0.0022 (11)	−0.0077 (11)
C20	0.0354 (14)	0.0232 (14)	0.0258 (13)	−0.0089 (11)	−0.0023 (11)	−0.0102 (11)
C21	0.0457 (16)	0.0197 (13)	0.0235 (13)	−0.0080 (11)	−0.0043 (11)	−0.0083 (11)
C22	0.0469 (16)	0.0258 (15)	0.0300 (14)	−0.0127 (12)	−0.0069 (12)	−0.0121 (12)
C23	0.0470 (16)	0.0283 (15)	0.0272 (13)	−0.0104 (12)	−0.0108 (12)	−0.0106 (12)
C24	0.0422 (15)	0.0213 (14)	0.0254 (13)	−0.0069 (11)	−0.0070 (11)	−0.0073 (11)

F1—C10	1.333 (3)	C4—C5	1.423 (4)
F2—C10	1.329 (3)	C4—C9	1.425 (4)
F3—C10	1.318 (3)	C5—C6	1.359 (4)
F4—C11	1.346 (3)	C5—H5	0.9500
F5—C11	1.338 (3)	C6—C7	1.414 (4)
F6—C11	1.345 (3)	C6—H6A	0.9500
O1—C12	1.417 (3)	C7—C8	1.367 (4)
O1—H1	0.839 (10)	C7—H7	0.9500
O2—C18	1.249 (3)	C8—C9	1.419 (4)
O3—C18	1.248 (3)	C8—C11	1.501 (4)
O4—N3	1.223 (3)	C12—C13	1.540 (3)
O5—N3	1.230 (3)	C12—H12A	1.0000
O1W—H1W1	0.843 (10)	C13—C17	1.523 (4)
O1W—H1W2	0.843 (10)	C13—H13	1.0000
O2W—H2W1	0.849 (10)	C14—C15	1.516 (4)
O2W—H2W2	0.845 (10)	C14—H14A	0.9900
O3W—H2W2	1.36 (5)	C14—H14B	0.9900
O3W—H3W1	0.843 (10)	C15—C16	1.532 (4)
O3W—H3W2	0.843 (10)	C15—H15A	0.9900
N1—C1	1.307 (3)	C15—H15B	0.9900
N1—C9	1.370 (3)	C16—C17	1.518 (4)
N2—C14	1.499 (3)	C16—H16A	0.9900
N2—C13	1.502 (3)	C16—H16B	0.9900
N2—H21	0.885 (10)	C17—H17A	0.9900
N2—H22	0.886 (10)	C17—H17B	0.9900
N3—C21	1.481 (3)	C18—C19	1.513 (4)
N4—C23	1.374 (4)	C19—C24	1.384 (4)
N4—H41	0.881 (10)	C19—C20	1.389 (4)
N4—H42	0.877 (10)	C20—C21	1.384 (3)
C1—C2	1.409 (4)	C20—H20	0.9500
C1—C10	1.506 (4)	C21—C22	1.368 (4)
C2—C3	1.382 (4)	C22—C23	1.399 (4)
C2—H2A	0.9500	C22—H22A	0.9500
C3—C4	1.420 (4)	C23—C24	1.399 (4)
C3—C12	1.520 (3)	C24—H24	0.9500
C12—O1—H1	105 (2)	O1—C12—C3	111.4 (2)
H1W1—O1W—H1W2	108.9 (18)	O1—C12—C13	108.89 (19)
H2W1—O2W—H2W2	107.6 (17)	C3—C12—C13	110.1 (2)
H2W2—O3W—H3W1	114 (6)	O1—C12—H12A	108.8
H2W2—O3W—H3W2	49 (6)	C3—C12—H12A	108.8
H3W1—O3W—H3W2	108.9 (18)	C13—C12—H12A	108.8
C1—N1—C9	116.9 (2)	N2—C13—C17	109.3 (2)
C14—N2—C13	113.7 (2)	N2—C13—C12	106.8 (2)
C14—N2—H21	108.8 (18)	C17—C13—C12	115.0 (2)
C13—N2—H21	103.5 (19)	N2—C13—H13	108.5
C14—N2—H22	105.2 (18)	C17—C13—H13	108.5
C13—N2—H22	112.4 (19)	C12—C13—H13	108.5
H21—N2—H22	113 (3)	N2—C14—C15	111.1 (2)
O4—N3—O5	122.9 (2)	N2—C14—H14A	109.4
O4—N3—C21	119.5 (2)	C15—C14—H14A	109.4
O5—N3—C21	117.6 (2)	N2—C14—H14B	109.4
C23—N4—H41	114 (2)	C15—C14—H14B	109.4
C23—N4—H42	118 (2)	H14A—C14—H14B	108.0
H41—N4—H42	117 (3)	C14—C15—C16	110.9 (2)
N1—C1—C2	125.9 (2)	C14—C15—H15A	109.5
N1—C1—C10	114.0 (2)	C16—C15—H15A	109.5
C2—C1—C10	120.1 (2)	C14—C15—H15B	109.5
C3—C2—C1	118.1 (2)	C16—C15—H15B	109.5
C3—C2—H2A	121.0	H15A—C15—H15B	108.1
C1—C2—H2A	121.0	C17—C16—C15	110.0 (2)
C2—C3—C4	118.5 (2)	C17—C16—H16A	109.7
C2—C3—C12	119.6 (2)	C15—C16—H16A	109.7
C4—C3—C12	121.8 (2)	C17—C16—H16B	109.7
C3—C4—C5	123.5 (2)	C15—C16—H16B	109.7
C3—C4—C9	118.3 (2)	H16A—C16—H16B	108.2
C5—C4—C9	118.2 (2)	C16—C17—C13	111.5 (2)
C6—C5—C4	120.8 (2)	C16—C17—H17A	109.3
C6—C5—H5	119.6	C13—C17—H17A	109.3
C4—C5—H5	119.6	C16—C17—H17B	109.3
C5—C6—C7	120.8 (2)	C13—C17—H17B	109.3
C5—C6—H6A	119.6	H17A—C17—H17B	108.0
C7—C6—H6A	119.6	O3—C18—O2	123.9 (2)
C8—C7—C6	120.3 (2)	O3—C18—C19	117.8 (2)
C8—C7—H7	119.9	O2—C18—C19	118.3 (2)
C6—C7—H7	119.9	C24—C19—C20	120.2 (2)
C7—C8—C9	120.2 (2)	C24—C19—C18	119.9 (2)
C7—C8—C11	119.6 (2)	C20—C19—C18	119.8 (2)
C9—C8—C11	120.1 (2)	C21—C20—C19	117.0 (2)
N1—C9—C8	118.1 (2)	C21—C20—H20	121.5
N1—C9—C4	122.2 (2)	C19—C20—H20	121.5
C8—C9—C4	119.6 (2)	C22—C21—C20	124.0 (2)
F3—C10—F2	108.0 (2)	C22—C21—N3	117.7 (2)
F3—C10—F1	106.2 (2)	C20—C21—N3	118.2 (2)
F2—C10—F1	105.0 (2)	C21—C22—C23	119.0 (2)
F3—C10—C1	112.7 (2)	C21—C22—H22A	120.5
F2—C10—C1	112.3 (2)	C23—C22—H22A	120.5
F1—C10—C1	112.1 (2)	N4—C23—C24	120.7 (2)
F5—C11—F6	106.4 (2)	N4—C23—C22	121.4 (2)
F5—C11—F4	106.9 (2)	C24—C23—C22	117.8 (2)
F6—C11—F4	105.7 (2)	C19—C24—C23	121.9 (2)
F5—C11—C8	113.6 (2)	C19—C24—H24	119.1
F6—C11—C8	112.1 (2)	C23—C24—H24	119.1
F4—C11—C8	111.6 (2)
C9—N1—C1—C2	3.1 (4)	C9—C8—C11—F4	61.3 (3)
C9—N1—C1—C10	−178.5 (2)	C2—C3—C12—O1	18.0 (3)
N1—C1—C2—C3	−2.3 (4)	C4—C3—C12—O1	−164.9 (2)
C10—C1—C2—C3	179.3 (2)	C2—C3—C12—C13	−102.9 (3)
C1—C2—C3—C4	−0.9 (3)	C4—C3—C12—C13	74.2 (3)
C1—C2—C3—C12	176.3 (2)	C14—N2—C13—C17	−55.4 (3)
C2—C3—C4—C5	−177.6 (2)	C14—N2—C13—C12	179.6 (2)
C12—C3—C4—C5	5.3 (4)	O1—C12—C13—N2	66.0 (2)
C2—C3—C4—C9	3.0 (3)	C3—C12—C13—N2	−171.6 (2)
C12—C3—C4—C9	−174.1 (2)	O1—C12—C13—C17	−55.4 (3)
C3—C4—C5—C6	−177.9 (2)	C3—C12—C13—C17	67.0 (3)
C9—C4—C5—C6	1.4 (4)	C13—N2—C14—C15	55.0 (3)
C4—C5—C6—C7	0.7 (4)	N2—C14—C15—C16	−54.2 (3)
C5—C6—C7—C8	−1.0 (4)	C14—C15—C16—C17	56.0 (3)
C6—C7—C8—C9	−0.9 (4)	C15—C16—C17—C13	−57.8 (3)
C6—C7—C8—C11	177.1 (2)	N2—C13—C17—C16	56.6 (3)
C1—N1—C9—C8	−179.1 (2)	C12—C13—C17—C16	176.7 (2)
C1—N1—C9—C4	−0.6 (3)	O3—C18—C19—C24	−178.8 (2)
C7—C8—C9—N1	−178.4 (2)	O2—C18—C19—C24	1.1 (3)
C11—C8—C9—N1	3.6 (3)	O3—C18—C19—C20	−0.2 (3)
C7—C8—C9—C4	3.0 (4)	O2—C18—C19—C20	179.7 (2)
C11—C8—C9—C4	−175.0 (2)	C24—C19—C20—C21	0.9 (3)
C3—C4—C9—N1	−2.3 (3)	C18—C19—C20—C21	−177.7 (2)
C5—C4—C9—N1	178.3 (2)	C19—C20—C21—C22	−0.8 (4)
C3—C4—C9—C8	176.1 (2)	C19—C20—C21—N3	178.9 (2)
C5—C4—C9—C8	−3.2 (3)	O4—N3—C21—C22	−176.4 (2)
N1—C1—C10—F3	170.9 (2)	O5—N3—C21—C22	4.3 (3)
C2—C1—C10—F3	−10.5 (3)	O4—N3—C21—C20	3.9 (3)
N1—C1—C10—F2	−66.8 (3)	O5—N3—C21—C20	−175.4 (2)
C2—C1—C10—F2	111.7 (3)	C20—C21—C22—C23	0.0 (4)
N1—C1—C10—F1	51.2 (3)	N3—C21—C22—C23	−179.6 (2)
C2—C1—C10—F1	−130.3 (2)	C21—C22—C23—N4	−177.1 (3)
C7—C8—C11—F5	122.3 (3)	C21—C22—C23—C24	0.6 (4)
C9—C8—C11—F5	−59.7 (3)	C20—C19—C24—C23	−0.3 (4)
C7—C8—C11—F6	1.7 (3)	C18—C19—C24—C23	178.3 (2)
C9—C8—C11—F6	179.7 (2)	N4—C23—C24—C19	177.3 (3)
C7—C8—C11—F4	−116.7 (3)	C22—C23—C24—C19	−0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84 (1)	1.83 (1)	2.669 (3)	178 (3)
N4—H41···O2i	0.88 (1)	2.04 (1)	2.900 (3)	164 (3)
N2—H21···O3ii	0.89 (1)	1.87 (1)	2.717 (3)	159 (3)
N4—H42···O5iii	0.88 (1)	2.27 (2)	3.101 (3)	159 (3)
N2—H22···O2W	0.89 (1)	2.05 (1)	2.916 (4)	165 (3)
N2—H22···O3W	0.89 (1)	1.98 (2)	2.727 (5)	141 (3)
OWw—H1W1···O1	0.84 (1)	2.08 (4)	2.867 (5)	156 (8)
O1W—H1W2···F6iv	0.84 (1)	2.47 (7)	2.867 (5)	110 (6)
O2W—H2W1···O1W	0.85 (1)	2.07 (2)	2.859 (6)	154 (4)
O2W—H2W2···O4v	0.85 (1)	2.30 (2)	3.119 (4)	165 (4)
O3W—H3W1···O3	0.84 (1)	2.21 (1)	3.049 (5)	174 (7)
O3W—H3W2···O4v	0.84 (1)	2.37 (3)	3.158 (5)	156 (7)
O3W—H3W2···O5v	0.84 (1)	2.32 (6)	3.016 (5)	140 (7)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84 (1)	1.83 (1)	2.669 (3)	178 (3)
N4—H41⋯O2i	0.88 (1)	2.04 (1)	2.900 (3)	164 (3)
N2—H21⋯O3ii	0.89 (1)	1.87 (1)	2.717 (3)	159 (3)
N4—H42⋯O5iii	0.88 (1)	2.27 (2)	3.101 (3)	159 (3)
N2—H22⋯O2W	0.89 (1)	2.05 (1)	2.916 (4)	165 (3)
N2—H22⋯O3W	0.89 (1)	1.98 (2)	2.727 (5)	141 (3)
OWw—H1W1⋯O1	0.84 (1)	2.08 (4)	2.867 (5)	156 (8)
O1W—H1W2⋯F6iv	0.84 (1)	2.47 (7)	2.867 (5)	110 (6)
O2W—H2W1⋯O1W	0.85 (1)	2.07 (2)	2.859 (6)	154 (4)
O2W—H2W2⋯O4v	0.85 (1)	2.30 (2)	3.119 (4)	165 (4)
O3W—H3W1⋯O3	0.84 (1)	2.21 (1)	3.049 (5)	174 (7)
O3W—H3W2⋯O4v	0.84 (1)	2.37 (3)	3.158 (5)	156 (7)
O3W—H3W2⋯O5v	0.84 (1)	2.32 (6)	3.016 (5)	140 (7)

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