Bis{4-[(2-hydroxy­benzyl­idine)hydra­zino]-8-(trifluoro­meth­yl)quinolinium} sulfate tetra­hydrate

The geometric parameters of the title compound, 2C₁₇H₁₃F₃N₃O⁺·SO₄²⁻·4H₂O, are in the usual ranges. There are two organic cations in the asymmetric unit with intra­molecular dihedral angles of 10.94 (9) and 7.14 (8)° between their aromatic ring mean planes. The crystal packing is stabilized by numerous N—H...O, O—H...O and O—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.041
• wR factor = 0.103
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O2W    -   H2WA   ...       1.03 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C14A   ..  O1'     ..       2.98 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         11

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

It is well known that the quinoline ring system is an important structural unit widely existing in alkaloids, therapeutics and synthetic analogues with interesting biological activities. A large variety of quinoline derivatives have been used as antimalarial, anti-inflammatory agents, antiasthmatic, antibacterial, antihypertensive and tyrokinase PDGF-RTK inhibiting agents. Furthermore, poly-substituted quinolines have been found to undergo hierarchical self-assembly into a variety of nano- and mesostructures with enhanced electronic and photonic functions.

Schiff bases are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. Moreover, Schiff bases are also known to have biological activities such as antimicrobial, antifungal, antitumor and as herbicides. Schiff bases have also been employed as ligands for complexation of metal ions. On the industrial scale, they have wide range of applications such as dyes and pigments.

The title compound, (I), a new Schiff base was synthesized and its crystal structure has been determined. The geometric parameters for (I) are in the usual ranges. There are two organic molecules in the asymmetric unit. The dihedral angles between the mean planes of their two aromatic ring systems are 10.94 (9)° and 7.14 (8)°, respectively. The crystal packing is stabilized by many N—H···O, O—H···O and O—H···N hydrogen bonds (Table 1).

Related literature

For related structures, see: 2'-(4-dimethylaminobenzylidene)pyrazine-2-carbohydrazide (Shi & Yuan, 2006); N'-(3-ethoxy-4-hydroxybenzylidene)isonicotino-hydrazide (Qian et al., 2006); 2'-(1,3-benzodioxol-5-ylmethylene)-2-methoxybenzo- hydrazide (Jing & Yu, 2007). For background literature, see: Roma et al. (2000); Maguire et al. (1994); Zhang & Jenekhe (2000); El-Masry et al. (2000); Pandey et al. (1999); Singh et al. (1988); Hodnett et al. (1970); Desai et al. (2001); Aydogan et al. (2001); Taggi et al. (2002).

For related literature, see: Zhang & Jenekhe (2000).

S2. Experimental

A mixture of 4-hydrazino-8-(trifluoromethyl)quinoline (1.13 g, 0.005 mol) and salicylaldehyde (0.61 g, 0.005 mol) in 15 ml of absolute ethanol containing 2 drops of 4 M sulfuric acid was refluxed for three hours. On cooling, the solid that separated was filtered and recrystallized from a (1:1 v/v) DMF & acetone mixture to yield crystals of (I) (m.p.: Above 523 K). Analysis for C₃₄H₃₄F₆N₆O₁₀S: Found (Calculated): C: 48.87 (48.99); H: 4.02 (4.08); N: 10.01 (10.09): S: 3.78% (3.84%)

S3. Refinement

The hydroxyphenyl ring of one molecule is disordered over two sites by a twofold rotation. Thus, the hydroxyl group is found in both ortho positions with site occupation factors of 0.778 (5) and 0.222 (5). H atoms were found in a difference map, but those bonded to C were refined using a riding model with C—H = 0.95 Å, and U_iso(H) = 1.2U_eq(C). H atoms bonded to O were freely refined, except for the minor component of the disordered hydroxyl H atoms which was refined using a riding model with O—H = 0.84 Å, and U_iso(H) = 1.2U_eq(O). The torsion angle about the C—O bond was allowed to refine.

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. Perspective view of (I); displacement ellipsoids are at the 50% probability level (arbitrary spheres for the H atoms).

Bis{4-[(2-hydroxybenzylidine)hydrazino]-8-(trifluoromethyl)quinolinium} sulfate tetrahydrate

Crystal data

2C17H13F3N3O^+·SO4^2^−·4H2O	Z = 2
Mr = 832.73	F(000) = 860
Triclinic, P1	Dx = 1.531 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.210 (2) Å	Cell parameters from 13707 reflections
b = 12.084 (2) Å	θ = 3.5–25.1°
c = 14.919 (3) Å	µ = 0.19 mm^−1
α = 84.64 (4)°	T = 173 K
β = 68.16 (4)°	Block, colourless
γ = 74.38 (3)°	0.24 × 0.23 × 0.19 mm
V = 1806.6 (8) Å^3

Data collection

Stoe IPDSII two-circle diffractometer	6759 independent reflections
Radiation source: fine-focus sealed tube	5130 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.059
ω scans	θmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −13→13
Tmin = 0.958, Tmax = 0.968	k = −14→14
25452 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0641P)^2] where P = (Fo^2 + 2Fc^2)/3
6759 reflections	(Δ/σ)max = 0.001
581 parameters	Δρmax = 0.22 e Å^−3
1 restraint	Δρmin = −0.43 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	1.3775 (2)	−0.22947 (19)	0.22630 (14)	0.0412 (7)	0.778 (5)
H1O	1.318 (5)	−0.172 (4)	0.211 (3)	0.081 (14)*	0.778 (5)
O1'	1.1034 (6)	−0.2603 (7)	0.5458 (5)	0.052 (3)	0.222 (5)
H1'	1.0558	−0.2007	0.5307	0.062*	0.222 (5)
N1	0.52896 (17)	0.09054 (14)	0.60698 (12)	0.0243 (3)
H1	0.454 (3)	0.116 (2)	0.6551 (18)	0.039 (7)*
N2	0.90860 (16)	−0.03268 (14)	0.40931 (13)	0.0241 (3)
H2	0.932 (2)	−0.0153 (19)	0.3513 (17)	0.027 (6)*
N3	1.00050 (15)	−0.11454 (14)	0.43810 (12)	0.0256 (4)
F1	0.31984 (13)	0.33610 (11)	0.61261 (10)	0.0474 (4)
F2	0.23127 (13)	0.30820 (15)	0.51411 (10)	0.0577 (4)
F3	0.26362 (11)	0.17934 (11)	0.61711 (9)	0.0396 (3)
C1	0.62302 (19)	0.01488 (17)	0.63286 (14)	0.0265 (4)
H1B	0.6005	−0.0089	0.6983	0.032*
C2	0.74900 (19)	−0.02940 (16)	0.56998 (13)	0.0252 (4)
H2B	0.8118	−0.0832	0.5914	0.030*
C3	0.78468 (18)	0.00583 (15)	0.47277 (13)	0.0213 (4)
C4	0.68345 (18)	0.08474 (15)	0.44273 (13)	0.0222 (4)
C5	0.55447 (18)	0.12711 (16)	0.51282 (13)	0.0218 (4)
C6	0.45417 (19)	0.20490 (16)	0.48440 (14)	0.0258 (4)
C7	0.4832 (2)	0.23695 (19)	0.38910 (15)	0.0335 (5)
H7	0.4167	0.2892	0.3703	0.040*
C8	0.6095 (2)	0.1934 (2)	0.31951 (15)	0.0383 (5)
H8	0.6270	0.2148	0.2538	0.046*
C9	0.7080 (2)	0.12030 (19)	0.34560 (14)	0.0308 (4)
H9	0.7937	0.0931	0.2980	0.037*
C10	0.3180 (2)	0.25691 (18)	0.55618 (15)	0.0301 (4)
C11	1.11525 (19)	−0.14833 (17)	0.37231 (14)	0.0272 (4)
H11	1.1313	−0.1141	0.3103	0.033*
C12	1.22281 (19)	−0.23742 (16)	0.38853 (14)	0.0250 (4)
C13	1.3457 (2)	−0.27358 (18)	0.31309 (15)	0.0308 (4)
H13	1.3620	−0.2358	0.2526	0.037*	0.222 (5)
C14	1.4443 (2)	−0.3651 (2)	0.32688 (18)	0.0395 (5)
H14	1.5272	−0.3896	0.2755	0.047*
C15	1.4219 (2)	−0.4200 (2)	0.41452 (18)	0.0428 (6)
H15	1.4887	−0.4834	0.4226	0.051*
C16	1.3023 (2)	−0.3834 (2)	0.49132 (18)	0.0432 (6)
H16	1.2880	−0.4202	0.5522	0.052*
C17	1.2044 (2)	−0.29276 (18)	0.47793 (16)	0.0339 (5)
H17	1.1229	−0.2675	0.5304	0.041*	0.778 (5)
O1A	0.32607 (15)	0.20844 (12)	0.20878 (11)	0.0347 (3)
H1OA	0.269 (3)	0.169 (2)	0.219 (2)	0.052 (8)*
N1A	0.85453 (16)	0.67791 (15)	−0.06464 (11)	0.0249 (3)
H1A	0.892 (2)	0.732 (2)	−0.0841 (17)	0.037 (7)*
N2A	0.64348 (17)	0.43207 (15)	0.04510 (12)	0.0271 (4)
H2A	0.676 (2)	0.358 (2)	0.0356 (17)	0.036 (6)*
N3A	0.51353 (16)	0.46623 (14)	0.11072 (11)	0.0272 (4)
F1A	1.26581 (13)	0.57259 (14)	−0.23741 (11)	0.0570 (4)
F2A	1.09414 (14)	0.68921 (14)	−0.25668 (10)	0.0513 (4)
F3A	1.12818 (13)	0.69213 (13)	−0.12537 (9)	0.0452 (3)
C1A	0.72595 (18)	0.70800 (17)	−0.00552 (13)	0.0253 (4)
H1A1	0.6845	0.7869	0.0101	0.030*
C2A	0.65299 (19)	0.62951 (17)	0.03271 (13)	0.0255 (4)
H2A1	0.5631	0.6539	0.0750	0.031*
C3A	0.71164 (19)	0.51209 (16)	0.00923 (13)	0.0243 (4)
C4A	0.85016 (19)	0.47867 (17)	−0.05538 (13)	0.0254 (4)
C5A	0.92011 (19)	0.56478 (17)	−0.09054 (13)	0.0249 (4)
C6A	1.0574 (2)	0.53261 (19)	−0.15102 (13)	0.0309 (5)
C7A	1.1190 (2)	0.4183 (2)	−0.17435 (15)	0.0387 (5)
H7A	1.2107	0.3967	−0.2134	0.046*
C8A	1.0493 (2)	0.3342 (2)	−0.14170 (16)	0.0411 (6)
H8A	1.0935	0.2562	−0.1595	0.049*
C9A	0.9176 (2)	0.36283 (18)	−0.08410 (15)	0.0344 (5)
H9A	0.8710	0.3046	−0.0631	0.041*
C10A	1.1356 (2)	0.6208 (2)	−0.19247 (14)	0.0339 (5)
C11A	0.4553 (2)	0.38410 (17)	0.14187 (14)	0.0277 (4)
H11A	0.5008	0.3080	0.1185	0.033*
C12A	0.3197 (2)	0.40731 (17)	0.21290 (14)	0.0269 (4)
C13A	0.2583 (2)	0.31612 (17)	0.24648 (15)	0.0288 (4)
C14A	0.1308 (2)	0.33696 (19)	0.31723 (16)	0.0346 (5)
H14A	0.0902	0.2752	0.3409	0.042*
C15A	0.0632 (2)	0.4472 (2)	0.35304 (18)	0.0400 (5)
H15A	−0.0232	0.4605	0.4014	0.048*
C16A	0.1210 (2)	0.5386 (2)	0.31869 (18)	0.0407 (5)
H16A	0.0739	0.6143	0.3425	0.049*
C17A	0.2477 (2)	0.51808 (19)	0.24951 (16)	0.0340 (5)
H17A	0.2871	0.5806	0.2262	0.041*
S1	0.86919 (5)	0.97050 (4)	0.84026 (3)	0.02299 (12)
O1S	0.98907 (14)	1.01484 (12)	0.79747 (10)	0.0305 (3)
O2S	0.87614 (14)	0.89968 (12)	0.92511 (10)	0.0322 (3)
O3S	0.85853 (15)	0.90418 (13)	0.76706 (10)	0.0355 (3)
O4S	0.75019 (14)	1.07005 (13)	0.87035 (11)	0.0379 (4)
O1W	0.2831 (2)	0.81279 (15)	0.96894 (15)	0.0537 (5)
H1WA	0.280 (3)	0.843 (3)	1.019 (3)	0.069 (10)*
H1WB	0.239 (4)	0.863 (3)	0.938 (3)	0.084 (11)*
O2W	0.50009 (19)	0.0371 (2)	0.89926 (14)	0.0581 (5)
H2WA	0.521 (8)	−0.051 (8)	0.906 (6)	0.26 (4)*
H2WB	0.582 (4)	0.054 (3)	0.893 (3)	0.095 (12)*
O3W	0.15544 (16)	0.01500 (14)	0.89528 (12)	0.0356 (4)
H3WA	0.125 (3)	0.047 (3)	0.949 (3)	0.069 (10)*
H3WB	0.091 (3)	0.022 (3)	0.873 (2)	0.069 (9)*
O4W	0.34561 (17)	0.13431 (16)	0.78822 (11)	0.0397 (4)
H4WA	0.395 (4)	0.111 (3)	0.818 (3)	0.089 (13)*
H4WB	0.283 (4)	0.093 (3)	0.817 (2)	0.074 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0259 (11)	0.0488 (13)	0.0276 (11)	0.0117 (9)	−0.0022 (8)	0.0072 (9)
O1'	0.019 (4)	0.076 (6)	0.032 (4)	0.010 (3)	0.000 (3)	0.031 (4)
N1	0.0198 (8)	0.0262 (8)	0.0223 (8)	−0.0021 (7)	−0.0045 (7)	−0.0034 (7)
N2	0.0205 (8)	0.0259 (9)	0.0237 (9)	−0.0008 (7)	−0.0095 (7)	0.0012 (7)
N3	0.0200 (8)	0.0256 (8)	0.0309 (9)	0.0001 (7)	−0.0127 (7)	−0.0009 (7)
F1	0.0396 (8)	0.0431 (8)	0.0521 (8)	−0.0084 (6)	−0.0038 (6)	−0.0251 (6)
F2	0.0277 (7)	0.0840 (11)	0.0456 (8)	0.0193 (7)	−0.0176 (6)	−0.0047 (7)
F3	0.0223 (6)	0.0421 (7)	0.0479 (7)	−0.0074 (5)	−0.0047 (6)	−0.0049 (6)
C1	0.0263 (10)	0.0266 (10)	0.0238 (9)	−0.0029 (8)	−0.0089 (8)	0.0013 (8)
C2	0.0240 (10)	0.0240 (10)	0.0257 (10)	−0.0005 (8)	−0.0108 (8)	0.0004 (8)
C3	0.0195 (9)	0.0190 (9)	0.0262 (9)	−0.0032 (7)	−0.0096 (8)	−0.0031 (7)
C4	0.0218 (9)	0.0218 (9)	0.0236 (9)	−0.0039 (7)	−0.0098 (8)	−0.0014 (7)
C5	0.0207 (9)	0.0215 (9)	0.0247 (9)	−0.0035 (7)	−0.0101 (8)	−0.0042 (7)
C6	0.0225 (10)	0.0261 (10)	0.0297 (10)	−0.0015 (8)	−0.0125 (8)	−0.0050 (8)
C7	0.0270 (11)	0.0377 (12)	0.0351 (11)	0.0020 (9)	−0.0177 (9)	0.0014 (9)
C8	0.0310 (12)	0.0522 (14)	0.0257 (11)	0.0006 (10)	−0.0123 (9)	0.0044 (10)
C9	0.0219 (10)	0.0393 (12)	0.0249 (10)	−0.0009 (9)	−0.0065 (8)	0.0014 (9)
C10	0.0253 (10)	0.0312 (11)	0.0346 (11)	−0.0002 (9)	−0.0155 (9)	−0.0043 (9)
C11	0.0245 (10)	0.0267 (10)	0.0283 (10)	−0.0016 (8)	−0.0104 (8)	0.0002 (8)
C12	0.0215 (10)	0.0213 (9)	0.0331 (10)	0.0000 (8)	−0.0140 (8)	−0.0032 (8)
C13	0.0257 (10)	0.0313 (11)	0.0346 (11)	0.0006 (8)	−0.0143 (9)	−0.0047 (9)
C14	0.0270 (11)	0.0409 (12)	0.0478 (13)	0.0072 (9)	−0.0181 (10)	−0.0140 (11)
C15	0.0383 (13)	0.0344 (12)	0.0598 (15)	0.0068 (10)	−0.0331 (12)	−0.0010 (11)
C16	0.0420 (14)	0.0413 (13)	0.0506 (14)	−0.0050 (11)	−0.0278 (12)	0.0109 (11)
C17	0.0287 (12)	0.0332 (11)	0.0401 (12)	−0.0039 (9)	−0.0162 (10)	0.0028 (9)
O1A	0.0327 (8)	0.0241 (7)	0.0488 (9)	−0.0058 (6)	−0.0182 (7)	0.0030 (6)
N1A	0.0222 (8)	0.0281 (9)	0.0211 (8)	−0.0020 (7)	−0.0075 (7)	0.0021 (7)
N2A	0.0290 (9)	0.0226 (9)	0.0272 (9)	−0.0015 (7)	−0.0104 (7)	−0.0013 (7)
N3A	0.0249 (9)	0.0294 (9)	0.0261 (8)	−0.0041 (7)	−0.0097 (7)	−0.0008 (7)
F1A	0.0204 (7)	0.0686 (10)	0.0597 (9)	−0.0010 (6)	0.0036 (6)	−0.0009 (8)
F2A	0.0483 (8)	0.0716 (10)	0.0438 (8)	−0.0236 (7)	−0.0285 (7)	0.0298 (7)
F3A	0.0381 (7)	0.0619 (9)	0.0347 (7)	−0.0152 (6)	−0.0101 (6)	−0.0003 (6)
C1A	0.0216 (9)	0.0273 (10)	0.0219 (9)	0.0025 (8)	−0.0072 (8)	−0.0039 (8)
C2A	0.0195 (9)	0.0280 (10)	0.0220 (9)	0.0016 (8)	−0.0047 (8)	−0.0020 (8)
C3A	0.0255 (10)	0.0271 (10)	0.0186 (9)	0.0008 (8)	−0.0111 (8)	−0.0002 (7)
C4A	0.0256 (10)	0.0279 (10)	0.0165 (9)	0.0040 (8)	−0.0080 (8)	−0.0005 (7)
C5A	0.0236 (10)	0.0298 (10)	0.0153 (8)	0.0042 (8)	−0.0085 (8)	0.0018 (7)
C6A	0.0237 (10)	0.0427 (12)	0.0183 (9)	0.0035 (9)	−0.0074 (8)	0.0012 (8)
C7A	0.0270 (11)	0.0473 (13)	0.0244 (10)	0.0120 (10)	−0.0044 (9)	−0.0017 (9)
C8A	0.0408 (13)	0.0332 (12)	0.0311 (11)	0.0118 (10)	−0.0063 (10)	−0.0039 (9)
C9A	0.0369 (12)	0.0288 (11)	0.0268 (10)	0.0049 (9)	−0.0083 (9)	−0.0014 (8)
C10A	0.0209 (10)	0.0493 (13)	0.0221 (10)	0.0024 (9)	−0.0059 (8)	0.0034 (9)
C11A	0.0319 (11)	0.0258 (10)	0.0311 (10)	−0.0060 (8)	−0.0193 (9)	0.0027 (8)
C12A	0.0292 (10)	0.0281 (10)	0.0298 (10)	−0.0076 (8)	−0.0178 (9)	0.0015 (8)
C13A	0.0312 (11)	0.0266 (10)	0.0364 (11)	−0.0063 (8)	−0.0227 (9)	0.0040 (8)
C14A	0.0302 (11)	0.0342 (11)	0.0446 (12)	−0.0119 (9)	−0.0174 (10)	0.0034 (9)
C15A	0.0270 (11)	0.0438 (13)	0.0490 (14)	−0.0090 (10)	−0.0117 (10)	−0.0068 (11)
C16A	0.0344 (12)	0.0354 (12)	0.0531 (14)	−0.0068 (10)	−0.0147 (11)	−0.0140 (10)
C17A	0.0348 (12)	0.0307 (11)	0.0418 (12)	−0.0116 (9)	−0.0168 (10)	−0.0027 (9)
S1	0.0192 (2)	0.0248 (2)	0.0228 (2)	−0.00320 (18)	−0.00665 (18)	−0.00071 (18)
O1S	0.0268 (7)	0.0397 (8)	0.0277 (7)	−0.0130 (6)	−0.0113 (6)	0.0064 (6)
O2S	0.0354 (8)	0.0335 (8)	0.0252 (7)	−0.0094 (6)	−0.0085 (6)	0.0039 (6)
O3S	0.0429 (9)	0.0366 (8)	0.0314 (8)	−0.0144 (7)	−0.0143 (7)	−0.0036 (6)
O4S	0.0277 (8)	0.0406 (9)	0.0373 (8)	0.0068 (7)	−0.0120 (7)	−0.0061 (7)
O1W	0.0787 (14)	0.0294 (9)	0.0528 (11)	0.0094 (9)	−0.0367 (11)	−0.0120 (8)
O2W	0.0390 (10)	0.0758 (14)	0.0551 (11)	−0.0068 (10)	−0.0198 (9)	0.0093 (10)
O3W	0.0351 (9)	0.0434 (9)	0.0304 (8)	−0.0074 (7)	−0.0153 (7)	−0.0025 (7)
O4W	0.0249 (8)	0.0587 (11)	0.0285 (8)	−0.0048 (8)	−0.0051 (7)	−0.0025 (7)

Geometric parameters (Å, º)

O1—C13	1.311 (3)	N2A—C3A	1.343 (3)
O1—H1O	0.90 (5)	N2A—N3A	1.393 (2)
O1'—C17	1.201 (6)	N2A—H2A	0.88 (3)
O1'—H1'	0.8400	N3A—C11A	1.290 (3)
N1—C1	1.347 (3)	F1A—C10A	1.344 (2)
N1—C5	1.380 (3)	F2A—C10A	1.339 (2)
N1—H1	0.88 (3)	F3A—C10A	1.346 (3)
N2—C3	1.341 (3)	C1A—C2A	1.365 (3)
N2—N3	1.388 (2)	C1A—H1A1	0.9500
N2—H2	0.83 (2)	C2A—C3A	1.410 (3)
N3—C11	1.280 (3)	C2A—H2A1	0.9500
F1—C10	1.341 (2)	C3A—C4A	1.458 (3)
F2—C10	1.335 (2)	C4A—C5A	1.416 (3)
F3—C10	1.347 (3)	C4A—C9A	1.420 (3)
C1—C2	1.365 (3)	C5A—C6A	1.430 (3)
C1—H1B	0.9500	C6A—C7A	1.380 (3)
C2—C3	1.410 (3)	C6A—C10A	1.505 (3)
C2—H2B	0.9500	C7A—C8A	1.389 (4)
C3—C4	1.454 (3)	C7A—H7A	0.9500
C4—C9	1.418 (3)	C8A—C9A	1.369 (3)
C4—C5	1.422 (3)	C8A—H8A	0.9500
C5—C6	1.428 (3)	C9A—H9A	0.9500
C6—C7	1.378 (3)	C11A—C12A	1.463 (3)
C6—C10	1.505 (3)	C11A—H11A	0.9500
C7—C8	1.402 (3)	C12A—C17A	1.403 (3)
C7—H7	0.9500	C12A—C13A	1.410 (3)
C8—C9	1.371 (3)	C13A—C14A	1.398 (3)
C8—H8	0.9500	C14A—C15A	1.387 (3)
C9—H9	0.9500	C14A—H14A	0.9500
C11—C12	1.463 (3)	C15A—C16A	1.391 (3)
C11—H11	0.9500	C15A—H15A	0.9500
C12—C13	1.404 (3)	C16A—C17A	1.383 (3)
C12—C17	1.404 (3)	C16A—H16A	0.9500
C13—C14	1.399 (3)	C17A—H17A	0.9500
C13—H13	0.9500	S1—O3S	1.4701 (15)
C14—C15	1.377 (4)	S1—O2S	1.4752 (15)
C14—H14	0.9500	S1—O1S	1.4786 (15)
C15—C16	1.392 (4)	S1—O4S	1.4897 (16)
C15—H15	0.9500	O1W—H1WA	0.85 (3)
C16—C17	1.386 (3)	O1W—H1WB	0.88 (4)
C16—H16	0.9500	O2W—H2WA	1.04 (9)
C17—H17	0.9500	O2W—H2WB	0.96 (4)
O1A—C13A	1.369 (3)	O3W—H3WA	0.83 (4)
O1A—H1OA	0.86 (3)	O3W—H3WB	0.88 (4)
N1A—C1A	1.349 (3)	O4W—H4WA	0.81 (4)
N1A—C5A	1.380 (3)	O4W—H4WB	0.91 (4)
N1A—H1A	0.85 (3)
C13—O1—H1O	120 (3)	C5A—N1A—H1A	122.5 (17)
C17—O1'—H1'	109.5	C3A—N2A—N3A	118.62 (17)
C1—N1—C5	121.24 (17)	C3A—N2A—H2A	125.6 (16)
C1—N1—H1	114.2 (16)	N3A—N2A—H2A	115.5 (16)
C5—N1—H1	124.5 (16)	C11A—N3A—N2A	114.67 (17)
C3—N2—N3	119.40 (17)	N1A—C1A—C2A	122.61 (18)
C3—N2—H2	123.2 (16)	N1A—C1A—H1A1	118.7
N3—N2—H2	117.1 (16)	C2A—C1A—H1A1	118.7
C11—N3—N2	115.17 (17)	C1A—C2A—C3A	119.73 (18)
N1—C1—C2	123.41 (18)	C1A—C2A—H2A1	120.1
N1—C1—H1B	118.3	C3A—C2A—H2A1	120.1
C2—C1—H1B	118.3	N2A—C3A—C2A	121.69 (18)
C1—C2—C3	119.09 (18)	N2A—C3A—C4A	120.16 (17)
C1—C2—H2B	120.5	C2A—C3A—C4A	118.16 (18)
C3—C2—H2B	120.5	C5A—C4A—C9A	118.79 (18)
N2—C3—C2	121.02 (17)	C5A—C4A—C3A	118.82 (17)
N2—C3—C4	120.64 (17)	C9A—C4A—C3A	122.40 (19)
C2—C3—C4	118.34 (17)	N1A—C5A—C4A	119.19 (17)
C9—C4—C5	118.53 (17)	N1A—C5A—C6A	121.44 (19)
C9—C4—C3	122.43 (17)	C4A—C5A—C6A	119.36 (18)
C5—C4—C3	119.04 (17)	C7A—C6A—C5A	119.4 (2)
N1—C5—C4	118.83 (17)	C7A—C6A—C10A	119.03 (19)
N1—C5—C6	121.51 (17)	C5A—C6A—C10A	121.59 (19)
C4—C5—C6	119.66 (17)	C6A—C7A—C8A	121.2 (2)
C7—C6—C5	119.53 (18)	C6A—C7A—H7A	119.4
C7—C6—C10	118.45 (18)	C8A—C7A—H7A	119.4
C5—C6—C10	121.99 (17)	C9A—C8A—C7A	120.6 (2)
C6—C7—C8	120.90 (19)	C9A—C8A—H8A	119.7
C6—C7—H7	119.5	C7A—C8A—H8A	119.7
C8—C7—H7	119.5	C8A—C9A—C4A	120.7 (2)
C9—C8—C7	120.48 (19)	C8A—C9A—H9A	119.7
C9—C8—H8	119.8	C4A—C9A—H9A	119.7
C7—C8—H8	119.8	F2A—C10A—F1A	106.92 (17)
C8—C9—C4	120.88 (19)	F2A—C10A—F3A	105.39 (18)
C8—C9—H9	119.6	F1A—C10A—F3A	105.61 (17)
C4—C9—H9	119.6	F2A—C10A—C6A	112.75 (17)
F2—C10—F1	106.85 (17)	F1A—C10A—C6A	112.27 (19)
F2—C10—F3	105.94 (17)	F3A—C10A—C6A	113.31 (16)
F1—C10—F3	105.51 (16)	N3A—C11A—C12A	120.48 (18)
F2—C10—C6	112.75 (17)	N3A—C11A—H11A	119.8
F1—C10—C6	112.05 (16)	C12A—C11A—H11A	119.8
F3—C10—C6	113.18 (17)	C17A—C12A—C13A	118.32 (19)
N3—C11—C12	122.74 (18)	C17A—C12A—C11A	122.14 (19)
N3—C11—H11	118.6	C13A—C12A—C11A	119.54 (18)
C12—C11—H11	118.6	O1A—C13A—C14A	121.48 (19)
C13—C12—C17	118.20 (18)	O1A—C13A—C12A	118.72 (19)
C13—C12—C11	120.45 (18)	C14A—C13A—C12A	119.80 (19)
C17—C12—C11	121.28 (18)	C15A—C14A—C13A	120.4 (2)
O1—C13—C14	114.9 (2)	C15A—C14A—H14A	119.8
O1—C13—C12	125.01 (19)	C13A—C14A—H14A	119.8
C14—C13—C12	120.1 (2)	C14A—C15A—C16A	120.5 (2)
C14—C13—H13	119.9	C14A—C15A—H15A	119.8
C12—C13—H13	119.9	C16A—C15A—H15A	119.8
C15—C14—C13	120.4 (2)	C17A—C16A—C15A	119.3 (2)
C15—C14—H14	119.8	C17A—C16A—H16A	120.4
C13—C14—H14	119.8	C15A—C16A—H16A	120.4
C14—C15—C16	120.6 (2)	C16A—C17A—C12A	121.7 (2)
C14—C15—H15	119.7	C16A—C17A—H17A	119.2
C16—C15—H15	119.7	C12A—C17A—H17A	119.2
C17—C16—C15	119.2 (2)	O3S—S1—O2S	111.38 (9)
C17—C16—H16	120.4	O3S—S1—O1S	109.47 (9)
C15—C16—H16	120.4	O2S—S1—O1S	109.60 (9)
O1'—C17—C16	118.2 (4)	O3S—S1—O4S	108.09 (9)
O1'—C17—C12	120.3 (4)	O2S—S1—O4S	109.72 (9)
C16—C17—C12	121.5 (2)	O1S—S1—O4S	108.52 (9)
C16—C17—H17	119.3	H1WA—O1W—H1WB	111 (3)
C12—C17—H17	119.3	H2WA—O2W—H2WB	103 (5)
C13A—O1A—H1OA	107.9 (19)	H3WA—O3W—H3WB	110 (3)
C1A—N1A—C5A	121.48 (18)	H4WA—O4W—H4WB	101 (3)
C1A—N1A—H1A	116.0 (17)
C3—N2—N3—C11	178.41 (17)	C11—C12—C17—C16	174.8 (2)
C5—N1—C1—C2	1.1 (3)	C3A—N2A—N3A—C11A	−179.78 (16)
N1—C1—C2—C3	0.7 (3)	C5A—N1A—C1A—C2A	0.4 (3)
N3—N2—C3—C2	4.5 (3)	N1A—C1A—C2A—C3A	−1.1 (3)
N3—N2—C3—C4	−175.15 (15)	N3A—N2A—C3A—C2A	−3.1 (3)
C1—C2—C3—N2	177.82 (17)	N3A—N2A—C3A—C4A	176.57 (15)
C1—C2—C3—C4	−2.5 (3)	C1A—C2A—C3A—N2A	−179.91 (17)
N2—C3—C4—C9	3.0 (3)	C1A—C2A—C3A—C4A	0.4 (3)
C2—C3—C4—C9	−176.66 (17)	N2A—C3A—C4A—C5A	−178.81 (16)
N2—C3—C4—C5	−177.67 (16)	C2A—C3A—C4A—C5A	0.9 (2)
C2—C3—C4—C5	2.6 (2)	N2A—C3A—C4A—C9A	1.0 (3)
C1—N1—C5—C4	−0.9 (3)	C2A—C3A—C4A—C9A	−179.33 (18)
C1—N1—C5—C6	178.29 (17)	C1A—N1A—C5A—C4A	1.0 (3)
C9—C4—C5—N1	178.35 (16)	C1A—N1A—C5A—C6A	−178.22 (17)
C3—C4—C5—N1	−1.0 (2)	C9A—C4A—C5A—N1A	178.65 (17)
C9—C4—C5—C6	−0.9 (3)	C3A—C4A—C5A—N1A	−1.6 (3)
C3—C4—C5—C6	179.83 (16)	C9A—C4A—C5A—C6A	−2.1 (3)
N1—C5—C6—C7	−178.44 (18)	C3A—C4A—C5A—C6A	177.65 (16)
C4—C5—C6—C7	0.7 (3)	N1A—C5A—C6A—C7A	179.49 (18)
N1—C5—C6—C10	3.8 (3)	C4A—C5A—C6A—C7A	0.3 (3)
C4—C5—C6—C10	−177.00 (17)	N1A—C5A—C6A—C10A	−2.4 (3)
C5—C6—C7—C8	0.6 (3)	C4A—C5A—C6A—C10A	178.40 (17)
C10—C6—C7—C8	178.4 (2)	C5A—C6A—C7A—C8A	1.3 (3)
C6—C7—C8—C9	−1.8 (4)	C10A—C6A—C7A—C8A	−176.86 (19)
C7—C8—C9—C4	1.7 (3)	C6A—C7A—C8A—C9A	−1.0 (3)
C5—C4—C9—C8	−0.3 (3)	C7A—C8A—C9A—C4A	−1.0 (3)
C3—C4—C9—C8	178.94 (19)	C5A—C4A—C9A—C8A	2.5 (3)
C7—C6—C10—F2	14.8 (3)	C3A—C4A—C9A—C8A	−177.29 (19)
C5—C6—C10—F2	−167.38 (17)	C7A—C6A—C10A—F2A	111.4 (2)
C7—C6—C10—F1	−105.8 (2)	C5A—C6A—C10A—F2A	−66.7 (2)
C5—C6—C10—F1	72.0 (2)	C7A—C6A—C10A—F1A	−9.4 (3)
C7—C6—C10—F3	135.07 (19)	C5A—C6A—C10A—F1A	172.50 (17)
C5—C6—C10—F3	−47.2 (2)	C7A—C6A—C10A—F3A	−128.9 (2)
N2—N3—C11—C12	−177.54 (16)	C5A—C6A—C10A—F3A	53.0 (2)
N3—C11—C12—C13	178.24 (18)	N2A—N3A—C11A—C12A	178.52 (15)
N3—C11—C12—C17	1.3 (3)	N3A—C11A—C12A—C17A	0.3 (3)
C17—C12—C13—O1	−179.4 (2)	N3A—C11A—C12A—C13A	−179.57 (17)
C11—C12—C13—O1	3.6 (3)	C17A—C12A—C13A—O1A	177.83 (17)
C17—C12—C13—C14	2.2 (3)	C11A—C12A—C13A—O1A	−2.3 (3)
C11—C12—C13—C14	−174.81 (18)	C17A—C12A—C13A—C14A	−2.4 (3)
O1—C13—C14—C15	−178.9 (2)	C11A—C12A—C13A—C14A	177.42 (17)
C12—C13—C14—C15	−0.3 (3)	O1A—C13A—C14A—C15A	−178.85 (19)
C13—C14—C15—C16	−1.7 (3)	C12A—C13A—C14A—C15A	1.4 (3)
C14—C15—C16—C17	1.7 (4)	C13A—C14A—C15A—C16A	0.4 (3)
C15—C16—C17—O1'	−177.9 (6)	C14A—C15A—C16A—C17A	−1.1 (4)
C15—C16—C17—C12	0.3 (3)	C15A—C16A—C17A—C12A	0.0 (3)
C13—C12—C17—O1'	175.9 (6)	C13A—C12A—C17A—C16A	1.7 (3)
C11—C12—C17—O1'	−7.1 (6)	C11A—C12A—C17A—C16A	−178.12 (19)
C13—C12—C17—C16	−2.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O4S^i	0.90 (5)	1.87 (5)	2.715 (3)	156 (4)
O1′—H1′···N3	0.84	1.84	2.602 (7)	149
N1—H1···O4W	0.88 (3)	1.90 (3)	2.713 (3)	153 (2)
N2—H2···O1S^i	0.83 (2)	2.06 (2)	2.873 (2)	166 (2)
O1A—H1OA···O3S^ii	0.86 (3)	1.81 (3)	2.671 (2)	175 (3)
N1A—H1A···O2S^iii	0.85 (3)	2.00 (3)	2.740 (2)	146 (2)
N2A—H2A···O1W^ii	0.88 (3)	1.99 (3)	2.855 (3)	169 (2)
O1W—H1WA···O4S^iv	0.85 (3)	1.92 (4)	2.752 (3)	170 (3)
O1W—H1WB···O3W^v	0.88 (4)	1.99 (4)	2.831 (3)	158 (3)
O2W—H2WA···O1A^vi	1.04 (9)	2.48 (9)	3.262 (3)	132 (6)
O2W—H2WB···O4S^vii	0.96 (4)	1.85 (4)	2.806 (3)	173 (3)
O3W—H3WA···O2S^viii	0.83 (4)	2.03 (4)	2.825 (2)	158 (3)
O3W—H3WB···O1S^ix	0.88 (4)	1.91 (4)	2.763 (2)	165 (3)
O4W—H4WA···O2W	0.81 (4)	1.99 (4)	2.793 (3)	171 (4)
O4W—H4WB···O3W	0.91 (4)	1.90 (4)	2.805 (3)	170 (3)

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