2-[(E)-1,1-Dioxo-2-(2,4,5-tri-fluoro-benz-yl)-3,4-di-hydro-2H-1,2-benzo-thia-zin-4-yl-idene]acetic acid.

In the asymmetric unit of the title compound, C17H12F3NO4S, there are two conformationally similar mol-ecules in which the heterocyclic thia-zine ring adopts a half-chair conformation, with the dihedral angle between the two benzene rings being 24.84 (8) and 37.42 (8)°. In the crystal, the mol-ecules form dimers through cyclic carb-oxy-lic acid O-H⋯O hydrogen-bonding associations [graph set R (2) 2(8)] and are extended into chains along [101] through weak C-H⋯Osulfin-yl hydrogen bonds [graph set R (2) 2(14)]..

Related literature

For pharmaceutical and biological properties of 1,2-benzo­thia­zines, see: Zia-ur-Rehman et al. (2005 ▶); Lombardino et al. (1971 ▶); Bihovsky et al. (2004 ▶); For synthetic details of the title compound, see: Parveen et al. (2014b ▶). For related structures, see: Yang et al. (2012 ▶); Parveen et al. (2014a ▶). For graph-set analysis, see: Etter et al. 1990 ▶).

Experimental

Crystal data

C17H12F3NO4S

M = 383.34

Triclinic,

a = 8.0028 (10) Å

b = 14.249 (2) Å

c = 15.076 (2) Å

α = 104.631 (8)°

β = 99.915 (6)°

γ = 104.237 (6)°

V = 1561.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 153 K

0.31 × 0.26 × 0.18 mm

Data collection

Rigaku AFC10/Saturn724+ CCD-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.932, T max = 0.964

20894 measured reflections

8293 independent reflections

6954 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.114

S = 1.00

8293 reflections

477 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear (Rigaku, 2008 ▶); data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 2008 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814013245/zs2301sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013245/zs2301Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814013245/zs2301Isup3.mol

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814013245/zs2301Isup4.cml

CCDC reference: 1007103

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H12F3NO4S	Z = 4
Mr = 383.34	F(000) = 784
Triclinic, P1	Dx = 1.631 Mg m−3
a = 8.0028 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.249 (2) Å	Cell parameters from 5221 reflections
c = 15.076 (2) Å	θ = 2.4–29.1°
α = 104.631 (8)°	µ = 0.27 mm−1
β = 99.915 (6)°	T = 153 K
γ = 104.237 (6)°	Prism, colourless
V = 1561.2 (4) Å3	0.31 × 0.26 × 0.18 mm

Rigaku AFC10/Saturn724+ CCD-detector diffractometer	8293 independent reflections
Radiation source: Rotating Anode	6954 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 28.5714 pixels mm-1	θmax = 29.1°, θmin = 2.7°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008)	k = −19→19
Tmin = 0.932, Tmax = 0.964	l = −20→20
20894 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.061P)2 + 0.226P] where P = (Fo2 + 2Fc2)/3
8293 reflections	(Δ/σ)max = 0.001
477 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.43 e Å−3

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

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

	x	y	z	Uiso*/Ueq
S1	0.73455 (5)	0.69761 (3)	0.55702 (3)	0.02391 (10)
S2	0.50292 (5)	0.87262 (3)	0.79867 (3)	0.02531 (10)
F1	0.58349 (14)	0.89772 (9)	0.31143 (8)	0.0450 (3)
F2	0.03716 (14)	0.93851 (8)	0.35868 (8)	0.0423 (3)
F3	0.08711 (14)	0.88184 (8)	0.51527 (8)	0.0391 (3)
F4	0.45408 (14)	0.54711 (9)	0.91587 (8)	0.0431 (3)
F5	1.01396 (15)	0.50243 (9)	0.90295 (8)	0.0469 (3)
F6	1.06588 (13)	0.63243 (8)	0.80223 (8)	0.0387 (3)
O1	0.63170 (15)	0.60907 (9)	0.57395 (8)	0.0311 (3)
O2	0.82039 (16)	0.78775 (9)	0.63550 (8)	0.0328 (3)
O4	0.99668 (15)	0.69914 (10)	0.24217 (8)	0.0337 (3)
O3	0.78052 (17)	0.70022 (12)	0.12780 (9)	0.0417 (3)
O5	0.63875 (15)	0.96931 (9)	0.83329 (9)	0.0335 (3)
O6	0.44968 (17)	0.82015 (11)	0.69925 (8)	0.0386 (3)
O7	0.26182 (16)	0.72184 (10)	1.15812 (9)	0.0334 (3)
O8	0.06107 (15)	0.74619 (10)	1.05181 (9)	0.0379 (3)
N1	0.60349 (16)	0.72401 (9)	0.47719 (9)	0.0224 (3)
N2	0.56830 (16)	0.79812 (10)	0.85392 (9)	0.0232 (3)
C1	0.89250 (19)	0.65910 (11)	0.49927 (11)	0.0233 (3)
C2	1.0447 (2)	0.65398 (12)	0.55604 (13)	0.0298 (3)
H2	1.0695	0.6801	0.6230	0.036*
C3	1.1599 (2)	0.61036 (13)	0.51375 (14)	0.0344 (4)
H3	1.2670	0.6092	0.5515	0.041*
C4	1.1179 (2)	0.56859 (13)	0.41639 (14)	0.0341 (4)
H4	1.1912	0.5334	0.3879	0.041*
C5	0.9703 (2)	0.57747 (12)	0.35992 (13)	0.0286 (3)
H5	0.9452	0.5495	0.2931	0.034*
C6	0.85747 (19)	0.62700 (11)	0.39983 (11)	0.0234 (3)
C7	0.70501 (19)	0.64394 (11)	0.34115 (11)	0.0232 (3)
C8	0.54758 (19)	0.64252 (11)	0.38476 (11)	0.0238 (3)
H8A	0.4509	0.6533	0.3417	0.029*
H8B	0.5017	0.5755	0.3940	0.029*
C9	0.6528 (2)	0.82967 (12)	0.47205 (12)	0.0273 (3)
H9A	0.7281	0.8352	0.4268	0.033*
H9B	0.7224	0.8774	0.5350	0.033*
C10	0.4876 (2)	0.85800 (11)	0.44047 (11)	0.0237 (3)
C11	0.4596 (2)	0.89144 (12)	0.36246 (12)	0.0291 (3)
C12	0.3112 (2)	0.91996 (13)	0.33337 (12)	0.0320 (4)
H12	0.2965	0.9430	0.2795	0.038*
C13	0.1865 (2)	0.91365 (12)	0.38516 (12)	0.0285 (3)
C14	0.2105 (2)	0.88278 (12)	0.46446 (12)	0.0266 (3)
C15	0.3584 (2)	0.85423 (11)	0.49217 (11)	0.0245 (3)
H15	0.3727	0.8319	0.5465	0.029*
C16	0.6974 (2)	0.66706 (12)	0.25983 (11)	0.0274 (3)
H16	0.5849	0.6697	0.2297	0.033*
C17	0.8406 (2)	0.68902 (12)	0.21090 (11)	0.0273 (3)
C18	0.31608 (19)	0.89025 (11)	0.83939 (11)	0.0224 (3)
C19	0.2095 (2)	0.93054 (13)	0.78660 (12)	0.0291 (3)
H19	0.2374	0.9444	0.7315	0.035*
C20	0.0627 (2)	0.95032 (13)	0.81459 (12)	0.0304 (3)
H20	−0.0118	0.9772	0.7787	0.036*
C21	0.0259 (2)	0.93060 (12)	0.89503 (12)	0.0282 (3)
H21	−0.0744	0.9447	0.9147	0.034*
C22	0.1323 (2)	0.89045 (11)	0.94806 (11)	0.0257 (3)
H22	0.1043	0.8787	1.0038	0.031*
C23	0.27989 (18)	0.86690 (10)	0.92127 (10)	0.0199 (3)
C24	0.39674 (19)	0.82390 (11)	0.97612 (10)	0.0207 (3)
C25	0.57919 (19)	0.83583 (12)	0.95578 (10)	0.0225 (3)
H25A	0.6501	0.9087	0.9807	0.027*
H25B	0.6418	0.7981	0.9894	0.027*
C26	0.4900 (2)	0.68674 (12)	0.80941 (12)	0.0276 (3)
H26A	0.4519	0.6705	0.7398	0.033*
H26B	0.3843	0.6616	0.8324	0.033*
C27	0.6278 (2)	0.63582 (11)	0.83449 (11)	0.0237 (3)
C28	0.6062 (2)	0.56868 (12)	0.88642 (12)	0.0286 (3)
C29	0.7309 (2)	0.52137 (13)	0.91045 (13)	0.0346 (4)
H29	0.7113	0.4752	0.9461	0.042*
C30	0.8843 (2)	0.54411 (13)	0.88054 (12)	0.0316 (4)
C31	0.9114 (2)	0.61120 (12)	0.82925 (11)	0.0266 (3)
C32	0.7862 (2)	0.65739 (11)	0.80590 (11)	0.0249 (3)
H32	0.8071	0.7037	0.7705	0.030*
C33	0.3679 (2)	0.77728 (11)	1.04221 (11)	0.0242 (3)
H33	0.4672	0.7587	1.0681	0.029*
C34	0.2146 (2)	0.74921 (11)	1.08260 (11)	0.0250 (3)
H7O	0.168 (3)	0.7121 (19)	1.1855 (17)	0.067 (8)*
H3O	0.865 (4)	0.720 (2)	0.1031 (19)	0.077 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.02321 (19)	0.02732 (19)	0.0232 (2)	0.00954 (14)	0.00707 (15)	0.00851 (14)
S2	0.02388 (19)	0.0386 (2)	0.0241 (2)	0.01631 (16)	0.01081 (15)	0.01787 (16)
F1	0.0420 (6)	0.0616 (7)	0.0486 (7)	0.0182 (5)	0.0274 (5)	0.0332 (6)
F2	0.0334 (6)	0.0458 (6)	0.0555 (7)	0.0206 (5)	0.0046 (5)	0.0252 (5)
F3	0.0347 (5)	0.0464 (6)	0.0510 (7)	0.0214 (5)	0.0237 (5)	0.0229 (5)
F4	0.0389 (6)	0.0487 (6)	0.0551 (7)	0.0143 (5)	0.0289 (5)	0.0267 (5)
F5	0.0471 (7)	0.0532 (7)	0.0505 (7)	0.0352 (6)	0.0067 (5)	0.0174 (6)
F6	0.0234 (5)	0.0409 (6)	0.0516 (7)	0.0125 (4)	0.0154 (5)	0.0070 (5)
O1	0.0305 (6)	0.0368 (6)	0.0326 (6)	0.0106 (5)	0.0128 (5)	0.0184 (5)
O2	0.0334 (6)	0.0353 (6)	0.0253 (6)	0.0123 (5)	0.0042 (5)	0.0023 (5)
O4	0.0260 (6)	0.0490 (7)	0.0280 (6)	0.0065 (5)	0.0093 (5)	0.0182 (5)
O3	0.0297 (7)	0.0699 (10)	0.0330 (7)	0.0114 (6)	0.0110 (5)	0.0304 (7)
O5	0.0253 (6)	0.0410 (7)	0.0467 (8)	0.0122 (5)	0.0143 (5)	0.0293 (6)
O6	0.0427 (7)	0.0659 (9)	0.0222 (6)	0.0336 (7)	0.0137 (5)	0.0188 (6)
O7	0.0327 (6)	0.0492 (7)	0.0321 (7)	0.0171 (6)	0.0153 (5)	0.0269 (6)
O8	0.0249 (6)	0.0608 (8)	0.0334 (7)	0.0077 (6)	0.0080 (5)	0.0283 (6)
N1	0.0209 (6)	0.0236 (6)	0.0241 (6)	0.0081 (5)	0.0066 (5)	0.0075 (5)
N2	0.0228 (6)	0.0309 (7)	0.0217 (6)	0.0132 (5)	0.0079 (5)	0.0112 (5)
C1	0.0214 (7)	0.0221 (7)	0.0293 (8)	0.0075 (5)	0.0089 (6)	0.0104 (6)
C2	0.0246 (8)	0.0301 (8)	0.0381 (9)	0.0092 (6)	0.0062 (7)	0.0166 (7)
C3	0.0222 (8)	0.0323 (8)	0.0563 (12)	0.0104 (7)	0.0107 (8)	0.0239 (8)
C4	0.0278 (8)	0.0303 (8)	0.0588 (12)	0.0144 (7)	0.0246 (8)	0.0240 (8)
C5	0.0290 (8)	0.0259 (7)	0.0379 (9)	0.0102 (6)	0.0182 (7)	0.0136 (7)
C6	0.0215 (7)	0.0198 (6)	0.0310 (8)	0.0056 (5)	0.0105 (6)	0.0094 (6)
C7	0.0211 (7)	0.0229 (7)	0.0237 (7)	0.0047 (5)	0.0073 (6)	0.0050 (6)
C8	0.0208 (7)	0.0268 (7)	0.0237 (8)	0.0063 (6)	0.0070 (6)	0.0076 (6)
C9	0.0226 (7)	0.0239 (7)	0.0368 (9)	0.0076 (6)	0.0074 (6)	0.0109 (6)
C10	0.0236 (7)	0.0205 (7)	0.0272 (8)	0.0060 (6)	0.0058 (6)	0.0088 (6)
C11	0.0287 (8)	0.0303 (8)	0.0325 (9)	0.0071 (6)	0.0133 (7)	0.0148 (7)
C12	0.0360 (9)	0.0315 (8)	0.0309 (9)	0.0082 (7)	0.0050 (7)	0.0180 (7)
C13	0.0249 (8)	0.0239 (7)	0.0367 (9)	0.0096 (6)	0.0013 (7)	0.0115 (6)
C14	0.0253 (7)	0.0252 (7)	0.0318 (9)	0.0089 (6)	0.0104 (6)	0.0100 (6)
C15	0.0273 (8)	0.0247 (7)	0.0255 (8)	0.0100 (6)	0.0079 (6)	0.0115 (6)
C16	0.0232 (7)	0.0315 (8)	0.0257 (8)	0.0049 (6)	0.0068 (6)	0.0085 (6)
C17	0.0278 (8)	0.0293 (8)	0.0235 (8)	0.0048 (6)	0.0073 (6)	0.0091 (6)
C18	0.0208 (7)	0.0274 (7)	0.0230 (7)	0.0107 (6)	0.0068 (6)	0.0105 (6)
C19	0.0292 (8)	0.0383 (9)	0.0268 (8)	0.0171 (7)	0.0073 (6)	0.0153 (7)
C20	0.0257 (8)	0.0353 (8)	0.0329 (9)	0.0160 (7)	0.0028 (7)	0.0117 (7)
C21	0.0200 (7)	0.0288 (8)	0.0360 (9)	0.0102 (6)	0.0077 (6)	0.0073 (7)
C22	0.0247 (7)	0.0261 (7)	0.0307 (8)	0.0099 (6)	0.0119 (6)	0.0107 (6)
C23	0.0191 (7)	0.0207 (6)	0.0205 (7)	0.0062 (5)	0.0048 (5)	0.0071 (5)
C24	0.0205 (7)	0.0223 (7)	0.0197 (7)	0.0065 (5)	0.0060 (5)	0.0063 (5)
C25	0.0209 (7)	0.0293 (7)	0.0214 (7)	0.0105 (6)	0.0059 (6)	0.0117 (6)
C26	0.0208 (7)	0.0298 (8)	0.0302 (8)	0.0085 (6)	0.0042 (6)	0.0065 (6)
C27	0.0213 (7)	0.0260 (7)	0.0234 (8)	0.0086 (6)	0.0063 (6)	0.0050 (6)
C28	0.0273 (8)	0.0301 (8)	0.0313 (9)	0.0090 (6)	0.0135 (7)	0.0101 (6)
C29	0.0439 (10)	0.0333 (9)	0.0340 (9)	0.0171 (8)	0.0124 (8)	0.0162 (7)
C30	0.0331 (9)	0.0328 (8)	0.0307 (9)	0.0194 (7)	0.0021 (7)	0.0075 (7)
C31	0.0196 (7)	0.0283 (8)	0.0293 (8)	0.0093 (6)	0.0075 (6)	0.0019 (6)
C32	0.0244 (7)	0.0254 (7)	0.0260 (8)	0.0084 (6)	0.0086 (6)	0.0077 (6)
C33	0.0240 (7)	0.0288 (7)	0.0228 (7)	0.0089 (6)	0.0080 (6)	0.0106 (6)
C34	0.0282 (8)	0.0263 (7)	0.0219 (7)	0.0067 (6)	0.0080 (6)	0.0102 (6)

S1—O2	1.4282 (12)	C9—H9A	0.9900
S1—O1	1.4347 (12)	C9—H9B	0.9900
S1—N1	1.6365 (13)	C10—C11	1.380 (2)
S1—C1	1.7708 (16)	C10—C15	1.396 (2)
S2—O6	1.4298 (13)	C11—C12	1.384 (2)
S2—O5	1.4342 (13)	C12—C13	1.369 (2)
S2—N2	1.6322 (13)	C12—H12	0.9500
S2—C18	1.7603 (15)	C13—C14	1.374 (2)
F1—C11	1.3553 (18)	C14—C15	1.376 (2)
F2—C13	1.3525 (18)	C15—H15	0.9500
F3—C14	1.3494 (18)	C16—C17	1.478 (2)
F4—C28	1.3578 (18)	C16—H16	0.9500
F5—C30	1.3519 (19)	C18—C19	1.388 (2)
F6—C31	1.3554 (17)	C18—C23	1.415 (2)
O4—C17	1.2156 (19)	C19—C20	1.383 (2)
O3—C17	1.326 (2)	C19—H19	0.9500
O3—H3O	0.85 (3)	C20—C21	1.375 (2)
O7—C34	1.3189 (19)	C20—H20	0.9500
O7—H7O	0.92 (3)	C21—C22	1.389 (2)
O8—C34	1.2224 (19)	C21—H21	0.9500
N1—C8	1.4841 (19)	C22—C23	1.401 (2)
N1—C9	1.4853 (19)	C22—H22	0.9500
N2—C25	1.4725 (19)	C23—C24	1.485 (2)
N2—C26	1.480 (2)	C24—C33	1.351 (2)
C1—C2	1.392 (2)	C24—C25	1.521 (2)
C1—C6	1.407 (2)	C25—H25A	0.9900
C2—C3	1.388 (2)	C25—H25B	0.9900
C2—H2	0.9500	C26—C27	1.508 (2)
C3—C4	1.383 (3)	C26—H26A	0.9900
C3—H3	0.9500	C26—H26B	0.9900
C4—C5	1.385 (2)	C27—C28	1.379 (2)
C4—H4	0.9500	C27—C32	1.397 (2)
C5—C6	1.401 (2)	C28—C29	1.383 (2)
C5—H5	0.9500	C29—C30	1.373 (2)
C6—C7	1.487 (2)	C29—H29	0.9500
C7—C16	1.343 (2)	C30—C31	1.374 (2)
C7—C8	1.516 (2)	C31—C32	1.372 (2)
C8—H8A	0.9900	C32—H32	0.9500
C8—H8B	0.9900	C33—C34	1.475 (2)
C9—C10	1.510 (2)	C33—H33	0.9500
O2—S1—O1	118.55 (7)	C13—C14—C15	120.66 (15)
O2—S1—N1	108.96 (7)	C14—C15—C10	120.07 (14)
O1—S1—N1	107.34 (7)	C14—C15—H15	120.0
O2—S1—C1	110.39 (7)	C10—C15—H15	120.0
O1—S1—C1	106.24 (7)	C7—C16—C17	128.74 (15)
N1—S1—C1	104.43 (7)	C7—C16—H16	115.6
O6—S2—O5	118.94 (8)	C17—C16—H16	115.6
O6—S2—N2	108.52 (7)	O4—C17—O3	122.46 (15)
O5—S2—N2	107.54 (7)	O4—C17—C16	125.63 (15)
O6—S2—C18	109.72 (7)	O3—C17—C16	111.87 (14)
O5—S2—C18	107.20 (7)	C19—C18—C23	122.65 (14)
N2—S2—C18	103.89 (7)	C19—C18—S2	115.21 (12)
C17—O3—H3O	111.3 (19)	C23—C18—S2	122.13 (11)
C34—O7—H7O	108.4 (16)	C20—C19—C18	119.63 (15)
C8—N1—C9	115.31 (12)	C20—C19—H19	120.2
C8—N1—S1	111.40 (10)	C18—C19—H19	120.2
C9—N1—S1	117.72 (10)	C21—C20—C19	119.25 (15)
C25—N2—C26	115.52 (12)	C21—C20—H20	120.4
C25—N2—S2	110.86 (10)	C19—C20—H20	120.4
C26—N2—S2	118.25 (10)	C20—C21—C22	121.26 (15)
C2—C1—C6	121.78 (14)	C20—C21—H21	119.4
C2—C1—S1	117.04 (12)	C22—C21—H21	119.4
C6—C1—S1	120.96 (11)	C21—C22—C23	121.56 (15)
C3—C2—C1	119.30 (17)	C21—C22—H22	119.2
C3—C2—H2	120.3	C23—C22—H22	119.2
C1—C2—H2	120.3	C22—C23—C18	115.61 (14)
C4—C3—C2	119.67 (16)	C22—C23—C24	123.11 (13)
C4—C3—H3	120.2	C18—C23—C24	121.24 (13)
C2—C3—H3	120.2	C33—C24—C23	130.34 (14)
C3—C4—C5	120.76 (16)	C33—C24—C25	114.86 (13)
C3—C4—H4	119.6	C23—C24—C25	114.79 (12)
C5—C4—H4	119.6	N2—C25—C24	112.43 (12)
C4—C5—C6	121.02 (16)	N2—C25—H25A	109.1
C4—C5—H5	119.5	C24—C25—H25A	109.1
C6—C5—H5	119.5	N2—C25—H25B	109.1
C5—C6—C1	116.90 (15)	C24—C25—H25B	109.1
C5—C6—C7	122.38 (15)	H25A—C25—H25B	107.8
C1—C6—C7	120.71 (13)	N2—C26—C27	108.89 (12)
C16—C7—C6	127.74 (14)	N2—C26—H26A	109.9
C16—C7—C8	117.96 (14)	C27—C26—H26A	109.9
C6—C7—C8	114.11 (13)	N2—C26—H26B	109.9
N1—C8—C7	109.66 (12)	C27—C26—H26B	109.9
N1—C8—H8A	109.7	H26A—C26—H26B	108.3
C7—C8—H8A	109.7	C28—C27—C32	117.47 (14)
N1—C8—H8B	109.7	C28—C27—C26	122.76 (14)
C7—C8—H8B	109.7	C32—C27—C26	119.77 (14)
H8A—C8—H8B	108.2	F4—C28—C27	118.67 (14)
N1—C9—C10	110.27 (12)	F4—C28—C29	117.60 (15)
N1—C9—H9A	109.6	C27—C28—C29	123.74 (15)
C10—C9—H9A	109.6	C30—C29—C28	117.02 (16)
N1—C9—H9B	109.6	C30—C29—H29	121.5
C10—C9—H9B	109.6	C28—C29—H29	121.5
H9A—C9—H9B	108.1	F5—C30—C29	120.43 (16)
C11—C10—C15	117.22 (14)	F5—C30—C31	118.55 (16)
C11—C10—C9	122.38 (14)	C29—C30—C31	121.00 (15)
C15—C10—C9	120.36 (14)	F6—C31—C32	119.75 (15)
F1—C11—C10	118.92 (15)	F6—C31—C30	119.01 (14)
F1—C11—C12	117.63 (14)	C32—C31—C30	121.24 (15)
C10—C11—C12	123.44 (15)	C31—C32—C27	119.54 (15)
C13—C12—C11	117.47 (15)	C31—C32—H32	120.2
C13—C12—H12	121.3	C27—C32—H32	120.2
C11—C12—H12	121.3	C24—C33—C34	133.41 (15)
F2—C13—C12	119.91 (15)	C24—C33—H33	113.3
F2—C13—C14	118.98 (15)	C34—C33—H33	113.3
C12—C13—C14	121.11 (15)	O8—C34—O7	121.92 (14)
F3—C14—C13	118.81 (14)	O8—C34—C33	127.55 (14)
F3—C14—C15	120.53 (14)	O7—C34—C33	110.48 (14)
O2—S1—N1—C8	165.08 (10)	C11—C10—C15—C14	0.3 (2)
O1—S1—N1—C8	−65.38 (11)	C9—C10—C15—C14	178.24 (14)
C1—S1—N1—C8	47.13 (11)	C6—C7—C16—C17	−4.9 (3)
O2—S1—N1—C9	28.63 (13)	C8—C7—C16—C17	169.70 (15)
O1—S1—N1—C9	158.17 (11)	C7—C16—C17—O4	−7.5 (3)
C1—S1—N1—C9	−89.32 (12)	C7—C16—C17—O3	174.59 (16)
O6—S2—N2—C25	−164.94 (10)	O6—S2—C18—C19	−49.22 (15)
O5—S2—N2—C25	65.20 (11)	O5—S2—C18—C19	81.24 (13)
C18—S2—N2—C25	−48.23 (11)	N2—S2—C18—C19	−165.08 (12)
O6—S2—N2—C26	−28.22 (13)	O6—S2—C18—C23	132.05 (13)
O5—S2—N2—C26	−158.09 (11)	O5—S2—C18—C23	−97.48 (13)
C18—S2—N2—C26	88.48 (12)	N2—S2—C18—C23	16.19 (14)
O2—S1—C1—C2	48.83 (14)	C23—C18—C19—C20	0.8 (2)
O1—S1—C1—C2	−80.91 (13)	S2—C18—C19—C20	−177.93 (13)
N1—S1—C1—C2	165.80 (12)	C18—C19—C20—C21	0.6 (3)
O2—S1—C1—C6	−136.40 (12)	C19—C20—C21—C22	−0.6 (2)
O1—S1—C1—C6	93.86 (13)	C20—C21—C22—C23	−1.0 (2)
N1—S1—C1—C6	−19.43 (14)	C21—C22—C23—C18	2.3 (2)
C6—C1—C2—C3	−4.0 (2)	C21—C22—C23—C24	180.00 (14)
S1—C1—C2—C3	170.69 (12)	C19—C18—C23—C22	−2.2 (2)
C1—C2—C3—C4	−2.9 (2)	S2—C18—C23—C22	176.43 (11)
C2—C3—C4—C5	5.6 (2)	C19—C18—C23—C24	−179.98 (14)
C3—C4—C5—C6	−1.4 (2)	S2—C18—C23—C24	−1.3 (2)
C4—C5—C6—C1	−5.3 (2)	C22—C23—C24—C33	18.1 (2)
C4—C5—C6—C7	175.82 (14)	C18—C23—C24—C33	−164.34 (16)
C2—C1—C6—C5	8.0 (2)	C22—C23—C24—C25	−160.80 (13)
S1—C1—C6—C5	−166.50 (11)	C18—C23—C24—C25	16.81 (19)
C2—C1—C6—C7	−173.07 (14)	C26—N2—C25—C24	−67.74 (16)
S1—C1—C6—C7	12.41 (19)	S2—N2—C25—C24	70.24 (14)
C5—C6—C7—C16	−37.3 (2)	C33—C24—C25—N2	128.86 (14)
C1—C6—C7—C16	143.83 (16)	C23—C24—C25—N2	−52.10 (17)
C5—C6—C7—C8	147.93 (14)	C25—N2—C26—C27	−77.84 (15)
C1—C6—C7—C8	−30.93 (19)	S2—N2—C26—C27	147.39 (11)
C9—N1—C8—C7	67.11 (16)	N2—C26—C27—C28	117.32 (16)
S1—N1—C8—C7	−70.46 (14)	N2—C26—C27—C32	−61.75 (19)
C16—C7—C8—N1	−115.16 (15)	C32—C27—C28—F4	179.40 (14)
C6—C7—C8—N1	60.14 (16)	C26—C27—C28—F4	0.3 (2)
C8—N1—C9—C10	76.81 (16)	C32—C27—C28—C29	−0.7 (2)
S1—N1—C9—C10	−148.39 (11)	C26—C27—C28—C29	−179.81 (16)
N1—C9—C10—C11	−124.09 (16)	F4—C28—C29—C30	−179.77 (15)
N1—C9—C10—C15	58.04 (19)	C27—C28—C29—C30	0.3 (3)
C15—C10—C11—F1	178.93 (14)	C28—C29—C30—F5	178.65 (15)
C9—C10—C11—F1	1.0 (2)	C28—C29—C30—C31	0.1 (3)
C15—C10—C11—C12	−0.6 (2)	F5—C30—C31—F6	0.6 (2)
C9—C10—C11—C12	−178.53 (15)	C29—C30—C31—F6	179.15 (15)
F1—C11—C12—C13	−179.90 (15)	F5—C30—C31—C32	−178.77 (14)
C10—C11—C12—C13	−0.4 (3)	C29—C30—C31—C32	−0.2 (3)
C11—C12—C13—F2	−178.60 (14)	F6—C31—C32—C27	−179.54 (13)
C11—C12—C13—C14	1.7 (2)	C30—C31—C32—C27	−0.2 (2)
F2—C13—C14—F3	−2.4 (2)	C28—C27—C32—C31	0.6 (2)
C12—C13—C14—F3	177.31 (15)	C26—C27—C32—C31	179.73 (14)
F2—C13—C14—C15	178.23 (14)	C23—C24—C33—C34	1.9 (3)
C12—C13—C14—C15	−2.1 (2)	C25—C24—C33—C34	−179.25 (15)
F3—C14—C15—C10	−178.34 (14)	C24—C33—C34—O8	14.6 (3)
C13—C14—C15—C10	1.0 (2)	C24—C33—C34—O7	−168.18 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O8i	0.85 (3)	1.86 (3)	2.7063 (17)	172 (3)
O7—H7O···O4ii	0.92 (3)	1.73 (3)	2.6473 (17)	177 (2)
C15—H15···O6	0.95	2.34	3.267 (2)	165
C32—H32···O2	0.95	2.61	3.539 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O8i	0.85 (3)	1.86 (3)	2.7063 (17)	172 (3)
O7—H7O⋯O4ii	0.92 (3)	1.73 (3)	2.6473 (17)	177 (2)
C15—H15⋯O6	0.95	2.34	3.267 (2)	165
C32—H32⋯O2	0.95	2.61	3.539 (2)	165

Symmetry codes: (i) ; (ii) .