1,1,1-Trifluoro-4-(thio-phen-2-yl)-4-[(2-{[4,4,4-trifluoro-3-oxo-1-(thio-phen-2-yl)but-1-en-1-yl]amino}-eth-yl)amino]-but-3-en-2-one.

The asymmetric unit of the diamine compound, C(18)H(14)F(3)N(2)O(2)S(2), consists of two mol-ecules; the C=C double bond has a Z configuration in the C(4)H(3)S-C=C-C(=O)-C segment. The -NH-CH(2)-CH(2)-NH chain adopts a twisted U-shape. The amino group is an intra-molecular hydrogen-bond donor to the carbonyl group; the intra-molecular hydrogen bond generates a six-membered ring. In both mol-ecules, the thienyl rings are disordered over two positions; the occupancies of the major components are 0.817 (4) and 0.778 (4) in one mol-ecule and 0.960 (4) and 0.665 (4) in the other. One of the trifluoro-methyl groups is disordered over two positions with the major component having 0.637 (8) occupancy.

Related literature

For the synthesis, see: Wang & Tong (1995 ▶). For related structures, see: Bresciani-Pahor et al. (1979 ▶); Haider et al. (1981 ▶).

Experimental

Crystal data

C18H14F6N2O2S2

M = 468.43

Orthorhombic,

a = 20.4520 (4) Å

b = 12.5201 (2) Å

c = 15.8328 (2) Å

V = 4054.16 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 100 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.906, T max = 0.936

40183 measured reflections

9198 independent reflections

8265 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.122

S = 1.05

9198 reflections

633 parameters

242 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.61 e Å−3

Δρmin = −0.59 e Å−3

Absolute structure: Flack (1983 ▶), 4340 Friedel pairs

Flack parameter: 0.01 (7)

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036889/xu5326sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036889/xu5326Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036889/xu5326Isup3.cml

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

C18H14F6N2O2S2	F(000) = 1904
Mr = 468.43	Dx = 1.535 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 16458 reflections
a = 20.4520 (4) Å	θ = 2.3–27.5°
b = 12.5201 (2) Å	µ = 0.33 mm−1
c = 15.8328 (2) Å	T = 100 K
V = 4054.16 (11) Å3	Block, light-yellow
Z = 8	0.30 × 0.25 × 0.20 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	9198 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	8265 reflections with I > 2σ(I)
Mirror	Rint = 0.037
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.3°
ω scans	h = −26→24
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −16→15
Tmin = 0.906, Tmax = 0.936	l = −20→20
40183 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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0629P)2 + 2.3648P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
9198 reflections	Δρmax = 0.61 e Å−3
633 parameters	Δρmin = −0.59 e Å−3
242 restraints	Absolute structure: Flack (1983), 4340 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (7)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.81914 (6)	0.35483 (9)	0.50113 (16)	0.0299 (3)	0.817 (4)
C3'	0.8183 (5)	0.3618 (12)	0.4772 (9)	0.030*	0.183 (4)
H3'	0.8582	0.4000	0.4718	0.036*	0.183 (4)
S2	0.77950 (7)	0.40257 (11)	0.05479 (16)	0.0309 (4)	0.778 (4)
C13'	0.7645 (6)	0.4026 (14)	0.0719 (9)	0.031*	0.222 (4)
H13'	0.8073	0.3795	0.0575	0.037*	0.222 (4)
S3	0.52193 (5)	0.51039 (8)	0.63447 (16)	0.0349 (3)	0.960 (4)
C21'	0.5388 (9)	0.502 (3)	0.617 (4)	0.035*	0.040 (4)
H21'	0.4987	0.4743	0.6380	0.042*	0.040 (4)
S4	0.63026 (8)	0.23117 (13)	0.98065 (17)	0.0337 (4)	0.665 (4)
C31'	0.6224 (5)	0.2405 (11)	0.9654 (7)	0.034*	0.335 (4)
H31'	0.6605	0.2696	0.9909	0.040*	0.335 (4)
C1	0.7728 (2)	0.2583 (3)	0.5476 (3)	0.0292 (10)	0.817 (4)
H1	0.7856	0.2198	0.5966	0.035*	0.817 (4)
C2'	0.8064 (7)	0.2803 (13)	0.5393 (9)	0.029*	0.183 (4)
H2'	0.8371	0.2574	0.5805	0.035*	0.183 (4)
C2	0.71492 (19)	0.2427 (3)	0.5062 (3)	0.0273 (9)	0.817 (4)
H2	0.6831	0.1907	0.5210	0.033*	0.817 (4)
C1'	0.7452 (8)	0.2410 (12)	0.5305 (9)	0.027*	0.183 (4)
H1'	0.7276	0.1863	0.5653	0.033*	0.183 (4)
C3	0.7094 (3)	0.3148 (5)	0.4387 (4)	0.0270 (14)	0.817 (4)
H3	0.6712	0.3196	0.4047	0.032*	0.817 (4)
S1'	0.7030 (3)	0.3001 (8)	0.4502 (6)	0.027*	0.183 (4)
C11	0.7226 (3)	0.4923 (5)	0.0199 (4)	0.0344 (13)	0.778 (4)
H11	0.7273	0.5338	−0.0300	0.041*	0.778 (4)
C12'	0.7283 (10)	0.478 (2)	0.0239 (13)	0.034*	0.222 (4)
H12'	0.7443	0.5110	−0.0261	0.041*	0.222 (4)
C12	0.6696 (3)	0.4975 (5)	0.0719 (3)	0.0329 (12)	0.778 (4)
H12	0.6334	0.5439	0.0634	0.039*	0.778 (4)
C11'	0.6679 (10)	0.4979 (18)	0.0575 (11)	0.033*	0.222 (4)
H11'	0.6370	0.5460	0.0339	0.039*	0.222 (4)
C13	0.6751 (3)	0.4259 (4)	0.1393 (4)	0.0283 (12)	0.778 (4)
H13	0.6422	0.4187	0.1812	0.034*	0.778 (4)
S2'	0.6554 (2)	0.4254 (6)	0.1468 (4)	0.028*	0.222 (4)
C19	0.5478 (2)	0.6236 (3)	0.5854 (3)	0.0439 (12)	0.960 (4)
H19	0.5209	0.6844	0.5761	0.053*	0.960 (4)
C20'	0.545 (2)	0.600 (5)	0.573 (6)	0.044*	0.040 (4)
H20'	0.5089	0.6463	0.5616	0.053*	0.040 (4)
C20	0.6113 (2)	0.6170 (3)	0.5612 (3)	0.0374 (10)	0.960 (4)
H20	0.6343	0.6723	0.5327	0.045*	0.960 (4)
C19'	0.607 (2)	0.621 (4)	0.549 (5)	0.037*	0.040 (4)
H19'	0.6205	0.6834	0.5193	0.045*	0.040 (4)
C21	0.6388 (2)	0.5186 (4)	0.5835 (3)	0.0277 (8)	0.960 (4)
H21	0.6828	0.5002	0.5711	0.033*	0.960 (4)
S3'	0.6590 (11)	0.521 (2)	0.580 (2)	0.028*	0.040 (4)
C29	0.5823 (3)	0.1198 (5)	0.9760 (5)	0.0365 (17)	0.665 (4)
H29	0.5894	0.0584	1.0101	0.044*	0.665 (4)
C30'	0.5976 (7)	0.1367 (11)	0.9825 (8)	0.037*	0.335 (4)
H30'	0.6171	0.0879	1.0210	0.044*	0.335 (4)
C30	0.5329 (3)	0.1272 (5)	0.9190 (5)	0.0352 (15)	0.665 (4)
H30	0.5029	0.0715	0.9063	0.042*	0.665 (4)
C29'	0.5429 (7)	0.1157 (11)	0.9377 (8)	0.035*	0.335 (4)
H29'	0.5193	0.0505	0.9407	0.042*	0.335 (4)
C31	0.5325 (5)	0.2282 (8)	0.8817 (8)	0.039 (2)	0.665 (4)
H31	0.4999	0.2503	0.8427	0.046*	0.665 (4)
S4'	0.5213 (3)	0.2209 (6)	0.8748 (4)	0.039*	0.335 (4)
F1	0.58969 (11)	0.6069 (2)	0.3032 (3)	0.0653 (9)
F2	0.63964 (14)	0.7449 (2)	0.3477 (3)	0.0697 (9)
F3	0.63082 (13)	0.7177 (3)	0.2175 (2)	0.0758 (11)
F4	0.58607 (10)	0.10854 (18)	0.2800 (3)	0.0557 (7)
F5	0.63759 (19)	0.0490 (4)	0.3863 (2)	0.1062 (16)
F6	0.64439 (12)	−0.02908 (19)	0.2702 (3)	0.0724 (10)
F7	0.4634 (2)	0.1221 (3)	0.5841 (4)	0.0691 (19)	0.637 (8)
F8	0.5383 (3)	0.0168 (6)	0.5542 (5)	0.118 (3)	0.637 (8)
F9	0.4967 (3)	0.0071 (5)	0.6696 (4)	0.088 (2)	0.637 (8)
F7'	0.4514 (3)	0.1011 (7)	0.6466 (7)	0.087 (3)	0.363 (8)
F8'	0.5011 (5)	0.0915 (7)	0.5354 (4)	0.071 (3)	0.363 (8)
F9'	0.5227 (3)	−0.0136 (4)	0.6325 (6)	0.050 (2)	0.363 (8)
F10	0.50376 (13)	0.7510 (2)	0.9026 (2)	0.0550 (7)
F11	0.46071 (15)	0.6715 (3)	0.7974 (2)	0.0724 (9)
F12	0.44353 (12)	0.6167 (2)	0.9230 (3)	0.0645 (8)
O1	0.74885 (10)	0.63817 (17)	0.2411 (2)	0.0245 (5)
O2	0.75368 (11)	0.10238 (17)	0.3191 (2)	0.0255 (5)
O3	0.61131 (12)	0.11162 (18)	0.6867 (2)	0.0287 (5)
O4	0.59885 (11)	0.62983 (18)	0.8317 (2)	0.0281 (5)
N1	0.81933 (13)	0.4767 (2)	0.3145 (2)	0.0214 (5)
H1N	0.8150 (17)	0.526 (2)	0.2758 (18)	0.026*
N2	0.80754 (13)	0.2661 (2)	0.2295 (2)	0.0227 (5)
H2N	0.8117 (18)	0.210 (2)	0.263 (2)	0.027*
N3	0.66015 (13)	0.3092 (2)	0.6906 (2)	0.0206 (5)
H3N	0.6634 (19)	0.2397 (11)	0.699 (2)	0.025*
N4	0.65239 (12)	0.4362 (2)	0.8506 (2)	0.0188 (5)
H4N	0.6551 (18)	0.5034 (12)	0.836 (2)	0.023*
C4	0.76321 (17)	0.3778 (2)	0.4254 (2)	0.0273 (7)
C5	0.76608 (15)	0.4627 (2)	0.3615 (2)	0.0218 (6)
C6	0.71094 (15)	0.5277 (3)	0.3520 (2)	0.0244 (6)
H6	0.6749	0.5164	0.3887	0.029*
C7	0.70615 (15)	0.6077 (2)	0.2919 (2)	0.0223 (6)
C8	0.64054 (16)	0.6680 (3)	0.2888 (3)	0.0308 (7)
C9	0.87353 (15)	0.4019 (2)	0.3033 (2)	0.0231 (6)
H9A	0.8760	0.3536	0.3527	0.028*
H9B	0.9152	0.4420	0.2998	0.028*
C10	0.86425 (15)	0.3358 (3)	0.2227 (2)	0.0230 (6)
H10A	0.8585	0.3844	0.1739	0.028*
H10B	0.9038	0.2922	0.2125	0.028*
C14	0.73144 (15)	0.3671 (2)	0.1403 (2)	0.0243 (6)
C15	0.74753 (16)	0.2808 (2)	0.2002 (2)	0.0218 (6)
C16	0.69566 (16)	0.2139 (3)	0.2243 (2)	0.0250 (6)
H16	0.6540	0.2252	0.1994	0.030*
C17	0.70247 (15)	0.1316 (3)	0.2830 (3)	0.0238 (6)
C18	0.64150 (18)	0.0659 (3)	0.3048 (3)	0.0358 (8)
C22	0.59719 (15)	0.4511 (2)	0.6247 (2)	0.0248 (6)
C23	0.60659 (15)	0.3393 (2)	0.6502 (2)	0.0213 (6)
C24	0.55877 (15)	0.2635 (3)	0.6291 (2)	0.0256 (6)
H24	0.5203	0.2865	0.6008	0.031*
C25	0.56605 (16)	0.1554 (3)	0.6486 (3)	0.0274 (7)
C26	0.51242 (19)	0.0802 (3)	0.6161 (3)	0.0467 (11)
C27	0.71201 (15)	0.3739 (2)	0.7275 (2)	0.0200 (6)
H27A	0.7079	0.4487	0.7080	0.024*
H27B	0.7552	0.3465	0.7092	0.024*
C28	0.70705 (15)	0.3695 (2)	0.8237 (2)	0.0194 (6)
H28A	0.7000	0.2950	0.8424	0.023*
H28B	0.7482	0.3958	0.8494	0.023*
C32	0.58421 (15)	0.2942 (2)	0.9067 (2)	0.0237 (6)
C33	0.59499 (15)	0.4057 (2)	0.8802 (2)	0.0195 (6)
C34	0.54391 (16)	0.4786 (3)	0.8887 (2)	0.0243 (6)
H34	0.5039	0.4554	0.9132	0.029*
C35	0.54967 (15)	0.5854 (3)	0.8622 (2)	0.0238 (6)
C36	0.48897 (16)	0.6564 (3)	0.8712 (3)	0.0331 (8)

	U11	U22	U33	U12	U13	U23
S1	0.0389 (6)	0.0307 (6)	0.0202 (5)	0.0018 (4)	−0.0086 (4)	0.0065 (4)
S2	0.0444 (8)	0.0286 (6)	0.0196 (6)	−0.0034 (5)	−0.0023 (4)	0.0044 (4)
S3	0.0345 (5)	0.0312 (5)	0.0388 (5)	0.0102 (4)	−0.0073 (4)	−0.0019 (4)
S4	0.0385 (8)	0.0278 (7)	0.0347 (8)	−0.0062 (6)	−0.0076 (6)	0.0157 (6)
C1	0.052 (3)	0.0195 (19)	0.0158 (17)	0.0066 (19)	0.0069 (18)	0.0055 (14)
C2	0.034 (2)	0.0191 (18)	0.029 (2)	0.0017 (16)	0.0095 (18)	0.0034 (16)
C3	0.028 (2)	0.009 (2)	0.044 (3)	−0.0054 (16)	0.021 (2)	0.0011 (19)
C11	0.064 (4)	0.017 (3)	0.022 (2)	−0.009 (2)	−0.019 (2)	0.0030 (16)
C12	0.052 (3)	0.020 (2)	0.027 (3)	−0.0032 (19)	−0.022 (2)	0.0014 (19)
C13	0.037 (3)	0.024 (2)	0.025 (2)	−0.009 (3)	−0.003 (3)	−0.0018 (17)
C19	0.071 (3)	0.0204 (19)	0.040 (2)	0.0077 (19)	−0.025 (2)	−0.0027 (17)
C20	0.066 (3)	0.0229 (18)	0.0238 (19)	−0.0040 (18)	−0.0130 (18)	0.0034 (14)
C21	0.030 (2)	0.031 (2)	0.0221 (16)	−0.004 (2)	−0.002 (2)	−0.0017 (13)
C29	0.040 (4)	0.018 (3)	0.051 (4)	−0.007 (2)	0.011 (3)	0.019 (3)
C30	0.031 (3)	0.024 (3)	0.050 (4)	−0.010 (2)	0.001 (3)	0.004 (3)
C31	0.039 (5)	0.018 (3)	0.058 (5)	0.002 (3)	−0.012 (3)	0.008 (3)
F1	0.0253 (11)	0.0377 (14)	0.133 (3)	0.0008 (10)	0.0128 (14)	0.0210 (15)
F2	0.0597 (17)	0.0509 (16)	0.098 (2)	0.0229 (14)	−0.0003 (17)	−0.0277 (16)
F3	0.0454 (15)	0.115 (3)	0.0672 (18)	0.0397 (16)	0.0135 (13)	0.0494 (18)
F4	0.0242 (10)	0.0285 (12)	0.114 (2)	0.0029 (8)	0.0065 (13)	0.0132 (13)
F5	0.083 (2)	0.180 (4)	0.0556 (18)	−0.080 (3)	0.0037 (16)	0.037 (2)
F6	0.0357 (12)	0.0205 (12)	0.161 (3)	−0.0042 (9)	0.0048 (17)	−0.0111 (15)
F7	0.041 (2)	0.052 (2)	0.115 (4)	−0.0208 (19)	−0.053 (3)	0.029 (3)
F8	0.105 (4)	0.119 (5)	0.131 (5)	−0.029 (4)	−0.014 (3)	−0.083 (4)
F9	0.057 (3)	0.096 (4)	0.110 (4)	−0.052 (3)	−0.032 (3)	0.056 (3)
F7'	0.055 (4)	0.083 (5)	0.122 (6)	−0.022 (4)	0.018 (4)	−0.015 (4)
F8'	0.097 (5)	0.064 (5)	0.052 (4)	−0.038 (4)	−0.033 (4)	0.009 (3)
F9'	0.039 (4)	0.029 (3)	0.081 (5)	−0.009 (3)	−0.030 (3)	0.000 (3)
F10	0.0432 (13)	0.0328 (13)	0.089 (2)	0.0075 (10)	0.0100 (13)	−0.0235 (13)
F11	0.0778 (19)	0.081 (2)	0.0579 (16)	0.0553 (18)	−0.0245 (15)	−0.0128 (16)
F12	0.0347 (13)	0.0500 (15)	0.109 (2)	0.0131 (11)	0.0295 (15)	0.0152 (16)
O1	0.0239 (11)	0.0206 (11)	0.0291 (11)	−0.0008 (8)	0.0029 (9)	0.0048 (9)
O2	0.0278 (11)	0.0187 (11)	0.0299 (11)	0.0014 (9)	0.0003 (9)	0.0029 (9)
O3	0.0288 (12)	0.0240 (12)	0.0332 (12)	−0.0046 (9)	−0.0100 (10)	0.0038 (10)
O4	0.0264 (11)	0.0207 (11)	0.0373 (12)	−0.0001 (9)	0.0027 (10)	0.0046 (9)
N1	0.0242 (12)	0.0166 (12)	0.0233 (13)	0.0012 (10)	−0.0013 (10)	0.0016 (10)
N2	0.0296 (14)	0.0164 (12)	0.0220 (12)	−0.0012 (10)	0.0006 (11)	0.0006 (10)
N3	0.0246 (13)	0.0159 (12)	0.0213 (12)	−0.0027 (10)	−0.0020 (10)	0.0002 (10)
N4	0.0206 (11)	0.0141 (12)	0.0219 (12)	−0.0004 (10)	0.0001 (10)	0.0007 (9)
C4	0.0436 (19)	0.0223 (16)	0.0159 (14)	0.0046 (14)	0.0039 (13)	0.0016 (12)
C5	0.0270 (15)	0.0193 (15)	0.0190 (13)	−0.0017 (12)	−0.0008 (12)	−0.0005 (11)
C6	0.0280 (15)	0.0221 (15)	0.0230 (15)	−0.0001 (13)	0.0070 (12)	0.0017 (12)
C7	0.0225 (14)	0.0201 (15)	0.0242 (14)	−0.0023 (11)	0.0001 (12)	−0.0018 (12)
C8	0.0259 (16)	0.0235 (16)	0.0429 (19)	0.0013 (13)	0.0060 (15)	0.0049 (15)
C9	0.0209 (14)	0.0219 (15)	0.0264 (15)	0.0024 (12)	−0.0025 (12)	0.0037 (12)
C10	0.0234 (14)	0.0211 (15)	0.0245 (14)	0.0008 (12)	0.0021 (12)	0.0037 (12)
C14	0.0333 (16)	0.0196 (14)	0.0199 (14)	−0.0010 (12)	−0.0051 (13)	−0.0011 (12)
C15	0.0295 (16)	0.0189 (15)	0.0170 (13)	0.0006 (12)	−0.0016 (12)	−0.0032 (11)
C16	0.0263 (15)	0.0236 (16)	0.0251 (15)	0.0018 (12)	−0.0044 (13)	−0.0019 (12)
C17	0.0258 (15)	0.0177 (14)	0.0279 (15)	−0.0011 (11)	0.0029 (13)	−0.0011 (12)
C18	0.0297 (17)	0.0284 (18)	0.049 (2)	−0.0022 (14)	−0.0015 (16)	0.0045 (16)
C22	0.0311 (16)	0.0238 (15)	0.0194 (14)	0.0014 (13)	−0.0072 (12)	0.0007 (12)
C23	0.0242 (14)	0.0215 (14)	0.0184 (13)	−0.0006 (12)	0.0000 (11)	0.0001 (11)
C24	0.0248 (15)	0.0259 (16)	0.0262 (15)	−0.0018 (12)	−0.0076 (13)	0.0019 (12)
C25	0.0268 (15)	0.0299 (17)	0.0255 (15)	−0.0051 (13)	−0.0056 (13)	0.0022 (13)
C26	0.048 (2)	0.032 (2)	0.060 (3)	−0.0172 (18)	−0.023 (2)	0.0123 (19)
C27	0.0207 (14)	0.0177 (14)	0.0217 (14)	−0.0024 (11)	−0.0018 (12)	−0.0019 (11)
C28	0.0207 (14)	0.0157 (13)	0.0219 (13)	0.0017 (11)	−0.0008 (11)	0.0002 (11)
C32	0.0250 (15)	0.0206 (15)	0.0256 (15)	−0.0001 (12)	0.0029 (12)	0.0034 (12)
C33	0.0215 (14)	0.0208 (14)	0.0163 (13)	−0.0045 (11)	−0.0008 (11)	−0.0004 (11)
C34	0.0207 (14)	0.0241 (16)	0.0279 (15)	−0.0020 (12)	0.0013 (12)	0.0044 (12)
C35	0.0223 (14)	0.0227 (16)	0.0264 (15)	0.0017 (12)	−0.0008 (12)	0.0002 (12)
C36	0.0260 (16)	0.0271 (18)	0.046 (2)	0.0035 (14)	0.0005 (15)	−0.0016 (15)

S1—C4	1.682 (3)	S4'—C32	1.659 (6)
S1—C1	1.704 (4)	F1—C8	1.311 (4)
C3'—C4	1.408 (10)	F2—C8	1.340 (5)
C3'—C2'	1.438 (11)	F3—C8	1.304 (4)
C3'—H3'	0.9500	F4—C18	1.313 (4)
S2—C11	1.710 (5)	F5—C18	1.310 (5)
S2—C14	1.731 (3)	F6—C18	1.310 (5)
C13'—C14	1.351 (10)	F7—C26	1.240 (5)
C13'—C12'	1.421 (11)	F8—C26	1.368 (6)
C13'—H13'	0.9500	F9—C26	1.288 (5)
S3—C19	1.701 (4)	F7'—C26	1.363 (6)
S3—C22	1.716 (3)	F8'—C26	1.306 (6)
C21'—C22	1.357 (12)	F9'—C26	1.222 (6)
C21'—C20'	1.420 (12)	F10—C36	1.318 (4)
C21'—H21'	0.9500	F11—C36	1.317 (5)
S4—C32	1.697 (3)	F12—C36	1.336 (5)
S4—C29	1.707 (5)	O1—C7	1.248 (4)
C31'—C32	1.387 (9)	O2—C17	1.248 (4)
C31'—C30'	1.422 (11)	O3—C25	1.233 (4)
C31'—H31'	0.9500	O4—C35	1.247 (4)
C1—C2	1.367 (6)	N1—C5	1.331 (4)
C1—H1	0.9500	N1—C9	1.462 (4)
C2'—C1'	1.352 (11)	N1—H1N	0.875 (12)
C2'—H2'	0.9500	N2—C15	1.325 (4)
C2—C3	1.404 (6)	N2—C10	1.455 (4)
C2—H2	0.9500	N2—H2N	0.878 (12)
C1'—S1'	1.705 (11)	N3—C23	1.323 (4)
C1'—H1'	0.9500	N3—C27	1.457 (4)
C3—C4	1.371 (5)	N3—H3N	0.882 (12)
C3—H3	0.9500	N4—C33	1.321 (4)
S1'—C4	1.618 (7)	N4—C28	1.459 (4)
C11—C12	1.362 (6)	N4—H4N	0.874 (12)
C11—H11	0.9500	C4—C5	1.468 (4)
C12'—C11'	1.368 (11)	C5—C6	1.399 (4)
C12'—H12'	0.9500	C6—C7	1.385 (4)
C12—C13	1.398 (6)	C6—H6	0.9500
C12—H12	0.9500	C7—C8	1.541 (4)
C11'—S2'	1.701 (11)	C9—C10	1.533 (4)
C11'—H11'	0.9500	C9—H9A	0.9900
C13—C14	1.367 (6)	C9—H9B	0.9900
C13—H13	0.9500	C10—H10A	0.9900
S2'—C14	1.722 (6)	C10—H10B	0.9900
C19—C20	1.358 (6)	C14—C15	1.476 (4)
C19—H19	0.9500	C15—C16	1.405 (4)
C20'—C19'	1.360 (12)	C16—C17	1.394 (5)
C20'—H20'	0.9500	C16—H16	0.9500
C20—C21	1.400 (5)	C17—C18	1.533 (5)
C20—H20	0.9500	C22—C23	1.470 (4)
C19'—S3'	1.709 (12)	C23—C24	1.402 (4)
C19'—H19'	0.9500	C24—C25	1.397 (5)
C21—C22	1.364 (5)	C24—H24	0.9500
C21—H21	0.9500	C25—C26	1.534 (5)
S3'—C22	1.697 (11)	C27—C28	1.528 (4)
C29—C30	1.357 (7)	C27—H27A	0.9900
C29—H29	0.9500	C27—H27B	0.9900
C30'—C29'	1.351 (11)	C28—H28A	0.9900
C30'—H30'	0.9500	C28—H28B	0.9900
C30—C31	1.396 (9)	C32—C33	1.474 (4)
C30—H30	0.9500	C33—C34	1.394 (4)
C29'—S4'	1.708 (10)	C34—C35	1.406 (4)
C29'—H29'	0.9500	C34—H34	0.9500
C31—C32	1.399 (7)	C35—C36	1.534 (4)
C31—H31	0.9500
C4—S1—C1	92.9 (2)	C5—C6—H6	118.3
C4—C3'—C2'	111.3 (7)	O1—C7—C6	128.0 (3)
C4—C3'—H3'	124.3	O1—C7—C8	116.0 (3)
C2'—C3'—H3'	124.3	C6—C7—C8	116.0 (3)
C11—S2—C14	92.0 (2)	F3—C8—F1	107.9 (3)
C14—C13'—C12'	112.7 (7)	F3—C8—F2	104.9 (3)
C14—C13'—H13'	123.6	F1—C8—F2	106.7 (3)
C12'—C13'—H13'	123.6	F3—C8—C7	113.2 (3)
C19—S3—C22	92.3 (2)	F1—C8—C7	113.6 (3)
C22—C21'—C20'	112.0 (9)	F2—C8—C7	110.0 (3)
C22—C21'—H21'	124.0	N1—C9—C10	110.7 (2)
C20'—C21'—H21'	124.0	N1—C9—H9A	109.5
C32—S4—C29	91.8 (2)	C10—C9—H9A	109.5
C30'—C31'—H31'	124.2	N1—C9—H9B	109.5
C2—C1—S1	112.0 (3)	C10—C9—H9B	109.5
C2—C1—H1	124.0	H9A—C9—H9B	108.1
S1—C1—H1	124.0	N2—C10—C9	111.1 (2)
C1'—C2'—C3'	110.2 (8)	N2—C10—H10A	109.4
C1'—C2'—H2'	124.9	C9—C10—H10A	109.4
C3'—C2'—H2'	124.9	N2—C10—H10B	109.4
C1—C2—C3	110.1 (4)	C9—C10—H10B	109.4
C1—C2—H2	124.9	H10A—C10—H10B	108.0
C3—C2—H2	124.9	C13'—C14—C15	130.1 (7)
C2'—C1'—S1'	112.8 (10)	C13—C14—C15	126.1 (3)
C2'—C1'—H1'	123.6	C13'—C14—S2'	111.2 (7)
S1'—C1'—H1'	123.6	C15—C14—S2'	118.2 (3)
C4—C3—C2	114.9 (4)	C13—C14—S2	109.4 (3)
C4—C3—H3	122.5	C15—C14—S2	124.3 (2)
C2—C3—H3	122.5	N2—C15—C16	121.5 (3)
C4—S1'—C1'	93.3 (6)	N2—C15—C14	122.2 (3)
C12—C11—S2	112.1 (4)	C16—C15—C14	116.3 (3)
C12—C11—H11	123.9	C17—C16—C15	123.1 (3)
S2—C11—H11	123.9	C17—C16—H16	118.5
C11'—C12'—C13'	112.5 (9)	C15—C16—H16	118.5
C11'—C12'—H12'	123.7	O2—C17—C16	127.3 (3)
C13'—C12'—H12'	123.7	O2—C17—C18	115.0 (3)
C11—C12—C13	111.6 (4)	C16—C17—C18	117.7 (3)
C11—C12—H12	124.2	F6—C18—F5	105.6 (4)
C13—C12—H12	124.2	F6—C18—F4	106.4 (3)
C12'—C11'—S2'	111.3 (10)	F5—C18—F4	107.9 (4)
C12'—C11'—H11'	124.4	F6—C18—C17	110.9 (3)
S2'—C11'—H11'	124.4	F5—C18—C17	111.0 (3)
C14—C13—C12	115.0 (4)	F4—C18—C17	114.6 (3)
C14—C13—H13	122.5	C21—C22—C23	129.7 (3)
C12—C13—H13	122.5	C23—C22—S3'	120.8 (11)
C11'—S2'—C14	92.3 (6)	C21—C22—S3	109.5 (3)
C20—C19—S3	112.1 (3)	C23—C22—S3	120.3 (2)
C20—C19—H19	124.0	N3—C23—C24	120.0 (3)
S3—C19—H19	124.0	N3—C23—C22	120.8 (3)
C19'—C20'—C21'	112.6 (9)	C24—C23—C22	119.2 (3)
C19'—C20'—H20'	123.7	C25—C24—C23	121.9 (3)
C21'—C20'—H20'	123.7	C25—C24—H24	119.0
C19—C20—C21	111.4 (4)	C23—C24—H24	119.0
C19—C20—H20	124.3	O3—C25—C24	128.2 (3)
C21—C20—H20	124.3	O3—C25—C26	115.3 (3)
C20'—C19'—S3'	111.2 (11)	C24—C25—C26	116.4 (3)
C20'—C19'—H19'	124.4	F7—C26—F9	111.5 (4)
S3'—C19'—H19'	124.4	F9'—C26—F8'	110.0 (5)
C22—C21—C20	114.6 (4)	F9'—C26—F7'	105.6 (5)
C22—C21—H21	122.7	F7—C26—F8	105.4 (4)
C20—C21—H21	122.7	F9—C26—F8	98.9 (4)
C30—C29—S4	113.6 (4)	F9'—C26—C25	113.3 (3)
C30—C29—H29	123.2	F7—C26—C25	117.1 (3)
S4—C29—H29	123.2	F9—C26—C25	113.3 (3)
C29'—C30'—C31'	111.9 (8)	F8'—C26—C25	112.8 (4)
C29'—C30'—H30'	124.0	F7'—C26—C25	114.7 (4)
C31'—C30'—H30'	124.0	F8—C26—C25	108.6 (4)
C29—C30—C31	110.3 (5)	N3—C27—C28	109.4 (2)
C29—C30—H30	124.8	N3—C27—H27A	109.8
C31—C30—H30	124.8	C28—C27—H27A	109.8
C30'—C29'—S4'	111.7 (10)	N3—C27—H27B	109.8
C30'—C29'—H29'	124.1	C28—C27—H27B	109.8
S4'—C29'—H29'	124.1	H27A—C27—H27B	108.2
C30—C31—C32	114.2 (5)	N4—C28—C27	108.7 (2)
C30—C31—H31	122.9	N4—C28—H28A	109.9
C32—C31—H31	122.9	C27—C28—H28A	109.9
C32—S4'—C29'	92.8 (6)	N4—C28—H28B	109.9
C5—N1—C9	127.1 (3)	C27—C28—H28B	109.9
C5—N1—H1N	114 (2)	H28A—C28—H28B	108.3
C9—N1—H1N	116 (2)	C31'—C32—C33	124.4 (6)
C15—N2—C10	129.0 (3)	C31—C32—C33	126.2 (4)
C15—N2—H2N	114 (2)	C33—C32—S4'	123.6 (3)
C10—N2—H2N	116 (2)	C31—C32—S4	109.9 (4)
C23—N3—C27	129.7 (3)	C33—C32—S4	123.6 (2)
C23—N3—H3N	114 (3)	S4'—C32—S4	112.5 (3)
C27—N3—H3N	116 (3)	N4—C33—C34	120.7 (3)
C33—N4—C28	128.2 (3)	N4—C33—C32	120.6 (3)
C33—N4—H4N	115 (2)	C34—C33—C32	118.7 (3)
C28—N4—H4N	115 (3)	C33—C34—C35	122.1 (3)
C3—C4—C5	123.7 (4)	C33—C34—H34	119.0
C3'—C4—C5	118.2 (7)	C35—C34—H34	119.0
C3'—C4—S1'	112.4 (7)	O4—C35—C34	127.4 (3)
C5—C4—S1'	129.3 (4)	O4—C35—C36	115.5 (3)
C3—C4—S1	109.8 (3)	C34—C35—C36	117.1 (3)
C5—C4—S1	126.0 (3)	F10—C36—F11	107.8 (3)
N1—C5—C6	121.5 (3)	F10—C36—F12	105.3 (3)
N1—C5—C4	120.9 (3)	F11—C36—F12	107.0 (3)
C6—C5—C4	117.6 (3)	F10—C36—C35	111.7 (3)
C7—C6—C5	123.5 (3)	F11—C36—C35	110.8 (3)
C7—C6—H6	118.3	F12—C36—C35	113.8 (3)
C4—S1—C1—C2	0.1 (3)	C14—C15—C16—C17	−177.3 (3)
C4—C3'—C2'—C1'	0.2 (5)	C15—C16—C17—O2	−3.3 (5)
S1—C1—C2—C3	−2.5 (5)	C15—C16—C17—C18	178.9 (3)
C3'—C2'—C1'—S1'	−0.1 (2)	O2—C17—C18—F6	−72.0 (4)
C1—C2—C3—C4	4.4 (7)	C16—C17—C18—F6	106.1 (4)
C2'—C1'—S1'—C4	−0.1 (2)	O2—C17—C18—F5	45.0 (5)
C14—S2—C11—C12	1.4 (4)	C16—C17—C18—F5	−136.9 (4)
C14—C13'—C12'—C11'	−0.1 (5)	O2—C17—C18—F4	167.5 (3)
S2—C11—C12—C13	−1.4 (5)	C16—C17—C18—F4	−14.3 (5)
C13'—C12'—C11'—S2'	0.0 (2)	C20'—C21'—C22—C21	−1.4 (16)
C11—C12—C13—C14	0.7 (6)	C20'—C21'—C22—C23	−166 (3)
C12'—C11'—S2'—C14	0.02 (18)	C20'—C21'—C22—S3'	0.0 (6)
C22—S3—C19—C20	0.7 (3)	C20—C21—C22—C23	173.5 (3)
C22—C21'—C20'—C19'	0.0 (5)	C20—C21—C22—S3'	−163 (9)
S3—C19—C20—C21	−0.3 (4)	C20—C21—C22—S3	0.9 (4)
C21'—C20'—C19'—S3'	0.0 (2)	C19'—S3'—C22—C21'	0.0 (4)
C19—C20—C21—C22	−0.4 (5)	C19—S3—C22—C21	−0.9 (3)
C20'—C19'—S3'—C22	−0.01 (19)	C19—S3—C22—C23	−174.3 (3)
C32—S4—C29—C30	1.2 (5)	C19—S3—C22—S3'	2.1 (15)
C32—C31'—C30'—C29'	0.0 (5)	C27—N3—C23—C24	−171.8 (3)
S4—C29—C30—C31	−3.1 (8)	C27—N3—C23—C22	9.9 (5)
C31'—C30'—C29'—S4'	0.0 (2)	C21'—C22—C23—N3	−150 (3)
C29—C30—C31—C32	4.0 (12)	C21—C22—C23—N3	48.7 (5)
C30'—C29'—S4'—C32	0.00 (19)	S3'—C22—C23—N3	44.2 (15)
C2—C3—C4—C3'	2.3 (11)	S3—C22—C23—N3	−139.5 (3)
C2—C3—C4—C5	−176.2 (4)	C21'—C22—C23—C24	31 (3)
C2—C3—C4—S1'	−12 (6)	C21—C22—C23—C24	−129.6 (4)
C2—C3—C4—S1	−4.3 (6)	S3'—C22—C23—C24	−134.1 (15)
C2'—C3'—C4—C3	−1.9 (9)	S3—C22—C23—C24	42.2 (4)
C2'—C3'—C4—C5	176.7 (5)	N3—C23—C24—C25	−0.9 (5)
C2'—C3'—C4—S1'	−0.2 (6)	C22—C23—C24—C25	177.4 (3)
C1'—S1'—C4—C3'	0.2 (4)	C23—C24—C25—O3	2.1 (6)
C1'—S1'—C4—C5	−176.4 (5)	C23—C24—C25—C26	−175.6 (3)
C1'—S1'—C4—S1	−6.0 (5)	O3—C25—C26—F9'	−0.5 (7)
C1—S1—C4—C3	2.3 (4)	C24—C25—C26—F9'	177.5 (6)
C1—S1—C4—C5	174.0 (3)	O3—C25—C26—F7	173.8 (5)
C1—S1—C4—S1'	3.2 (4)	C24—C25—C26—F7	−8.2 (6)
C9—N1—C5—C6	−164.6 (3)	O3—C25—C26—F9	41.8 (6)
C9—N1—C5—C4	15.3 (5)	C24—C25—C26—F9	−140.1 (5)
C3—C4—C5—N1	−138.4 (5)	O3—C25—C26—F8'	−126.4 (6)
C3'—C4—C5—N1	43.1 (7)	C24—C25—C26—F8'	51.7 (7)
S1'—C4—C5—N1	−140.6 (5)	O3—C25—C26—F7'	120.8 (7)
S1—C4—C5—N1	51.0 (4)	C24—C25—C26—F7'	−61.2 (7)
C3—C4—C5—C6	41.4 (6)	O3—C25—C26—F8	−67.0 (6)
C3'—C4—C5—C6	−137.1 (7)	C24—C25—C26—F8	111.0 (5)
S1'—C4—C5—C6	39.3 (6)	C23—N3—C27—C28	108.1 (3)
S1—C4—C5—C6	−129.1 (3)	C33—N4—C28—C27	107.6 (3)
N1—C5—C6—C7	2.6 (5)	N3—C27—C28—N4	−75.1 (3)
C4—C5—C6—C7	−177.3 (3)	C30'—C31'—C32—C31	−0.5 (10)
C5—C6—C7—O1	−3.7 (5)	C30'—C31'—C32—C33	175.9 (6)
C5—C6—C7—C8	177.7 (3)	C30'—C31'—C32—S4'	0.0 (6)
O1—C7—C8—F3	20.9 (5)	C30'—C31'—C32—S4	112 (20)
C6—C7—C8—F3	−160.3 (3)	C30—C31—C32—C31'	−1.4 (14)
O1—C7—C8—F1	144.5 (3)	C30—C31—C32—C33	−177.7 (6)
C6—C7—C8—F1	−36.8 (4)	C30—C31—C32—S4'	−171 (20)
O1—C7—C8—F2	−96.0 (4)	C30—C31—C32—S4	−3.1 (12)
C6—C7—C8—F2	82.7 (4)	C29'—S4'—C32—C31'	0.0 (4)
C5—N1—C9—C10	96.2 (4)	C29'—S4'—C32—C33	−175.9 (5)
C15—N2—C10—C9	98.3 (4)	C29'—S4'—C32—S4	−1.7 (5)
N1—C9—C10—N2	−65.9 (3)	C29—S4—C32—C31	1.0 (7)
C12'—C13'—C14—C13	−4.0 (7)	C29—S4—C32—C33	175.8 (4)
C12'—C13'—C14—C15	172.0 (10)	C29—S4—C32—S4'	1.6 (4)
C12'—C13'—C14—S2'	0.1 (6)	C28—N4—C33—C34	−168.3 (3)
C12—C13—C14—C13'	1.0 (11)	C28—N4—C33—C32	13.1 (4)
C12—C13—C14—C15	−175.2 (4)	C31'—C32—C33—N4	54.7 (7)
C12—C13—C14—S2	0.4 (6)	C31—C32—C33—N4	−129.5 (8)
C11'—S2'—C14—C13'	−0.1 (4)	S4'—C32—C33—N4	−129.9 (4)
C11'—S2'—C14—C15	−173.0 (9)	S4—C32—C33—N4	56.6 (4)
C11'—S2'—C14—S2	−1.2 (9)	C31'—C32—C33—C34	−123.9 (6)
C11—S2—C14—C13	−1.0 (4)	C31—C32—C33—C34	51.9 (9)
C11—S2—C14—C15	174.7 (3)	S4'—C32—C33—C34	51.5 (5)
C11—S2—C14—S2'	3.4 (4)	S4—C32—C33—C34	−122.1 (3)
C10—N2—C15—C16	−169.2 (3)	N4—C33—C34—C35	3.6 (5)
C10—N2—C15—C14	11.3 (5)	C32—C33—C34—C35	−177.8 (3)
C13'—C14—C15—N2	41.9 (11)	C33—C34—C35—O4	−2.6 (5)
C13—C14—C15—N2	−142.9 (4)	C33—C34—C35—C36	177.2 (3)
S2'—C14—C15—N2	−146.6 (4)	O4—C35—C36—F10	−44.5 (4)
S2—C14—C15—N2	42.2 (4)	C34—C35—C36—F10	135.7 (3)
C13'—C14—C15—C16	−137.6 (11)	O4—C35—C36—F11	75.8 (4)
C13—C14—C15—C16	37.6 (5)	C34—C35—C36—F11	−104.0 (4)
S2'—C14—C15—C16	33.9 (4)	O4—C35—C36—F12	−163.5 (3)
S2—C14—C15—C16	−137.3 (3)	C34—C35—C36—F12	16.6 (5)
N2—C15—C16—C17	3.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1	0.88 (1)	2.03 (3)	2.741 (3)	138 (3)
N2—H2n···O2	0.88 (1)	2.01 (3)	2.726 (3)	138 (3)
N3—H3n···O3	0.88 (1)	1.93 (3)	2.668 (3)	140 (3)
N4—H4n···O4	0.87 (1)	1.96 (3)	2.677 (3)	139 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1	0.88 (1)	2.03 (3)	2.741 (3)	138 (3)
N2—H2n⋯O2	0.88 (1)	2.01 (3)	2.726 (3)	138 (3)
N3—H3n⋯O3	0.88 (1)	1.93 (3)	2.668 (3)	140 (3)
N4—H4n⋯O4	0.87 (1)	1.96 (3)	2.677 (3)	139 (3)