Synthesis, crystal structures and anti-inflammatory activity of four 3,5-bis­(aryl­idene)-N-benzene­sulfonyl-4-piperidone derivatives

Li, N.; Bai, X.; Zhang, L.; Hou, Y.

doi:10.1107/S2053229618013232

Synthesis, crystal structures and anti-inflammatory activity of four 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives

3,5-Bis(arylidene)-4-piperidone (BAP) derivatives display good antitumour and anti-inflammatory activities because of their double α,β-unsaturated ketone structural characteristics. If N-benzenesulfonyl substituents are introduced into BAPs, the configuration of the BAPs would change significantly and their anti-inflammatory activities should improve. Four N-benzenesulfonyl BAPs, namely (3E,5E)-1-(4-methylbenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one dichloromethane monosolvate, C₂₈H₂₁F₆NO₃S·CH₂Cl₂, (4), (3E,5E)-1-(4-fluorobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one, C₂₇H₁₈F₇NO₃S, (5), (3E,5E)-1-(4-nitrobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one, C₂₇H₁₈F₆N₂O₅S, (6), and (3E,5E)-1-(4-cyanobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one dichloromethane monosolvate, C₂₈H₁₈F₆N₂O₃S·CH₂Cl₂, (7), were prepared by Claisen–Schmidt condensation and N-sulfonylation. They were characterized by NMR, FT–IR and HRMS (high resolution mass spectrometry). Single-crystal structure analysis reveals that the two 4-(trifluoromethyl)phenyl rings on both sides of the piperidone ring in (4)–(7) adopt an E stereochemistry of the olefinic double bonds. Molecules of both (4) and (6) are connected by hydrogen bonds into one-dimensional chains. In (5) and (7), pairs of adjacent molecules embrace through intermolecular hydrogen bonds to form a bimolecular combination, which are further extended into a two-dimensional sheet. The anti-inflammatory activity data reveal that (4)–(7) significantly inhibit LPS-induced interleukin (IL-6) and tumour necrosis factor (TNF-α) secretion. Most importantly, (6) and (7), with strong electron-withdrawing substituents, display more potential inhibitory effects than (4) and (5).

Keywords: 3,5-bis(arylidene)-4-piperidone; benzenesulfonyl; anti-inflammatory activity; LPS-induced interleukin; tumour necrosis factor secretion; inhibitory effects; crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618013232/sk3698sup1.cif Contains datablocks 4, 5, 6, 7, global
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618013232/sk36984sup2.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618013232/sk36985sup3.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618013232/sk36986sup4.cml Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229618013232/sk36987sup5.cml Supplementary material
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618013232/sk36984sup6.hkl Contains datablock 4
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618013232/sk36985sup7.hkl Contains datablock 5
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618013232/sk36986sup8.hkl Contains datablock 6
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229618013232/sk36987sup9.hkl Contains datablock 7

CCDC references: 1848378; 1848377; 1848376; 1848375

Computing details top

For all structures, data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(3E,5E)-1-(4-Fluorobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one dichloromethane monosolvate (4) top

Crystal data top

C₂₈H₂₁F₆NO₃S·CH₂Cl₂	F(000) = 1328
M_r = 650.44	D_x = 1.511 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.6718 (5) Å	Cell parameters from 9943 reflections
b = 23.5083 (12) Å	θ = 2.5–26.4°
c = 14.3939 (9) Å	µ = 0.37 mm⁻¹
β = 102.962 (2)°	T = 150 K
V = 2859.6 (3) Å³	Block, yellow
Z = 4	0.14 × 0.10 × 0.10 mm

Data collection top

Bruker SMART CCD area detector diffractometer	R_int = 0.062
Radiation source: sealed tube	θ_max = 26.4°, θ_min = 2.3°
phi and ω scans	h = −10→10
38920 measured reflections	k = −29→29
5852 independent reflections	l = −17→17
4236 reflections with I > 2σ(I)

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0541P)² + 2.6939P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
5852 reflections	Δρ_max = 0.69 e Å⁻³
408 parameters	Δρ_min = −0.65 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.6042 (2)	0.09574 (8)	0.02605 (13)	0.0343 (4)
C1	0.2119 (3)	0.02787 (10)	0.00437 (17)	0.0224 (5)
H1A	0.2169	−0.0110	−0.0211	0.027*
H1B	0.1468	0.0265	0.0527	0.027*
C2	0.3771 (3)	0.04750 (9)	0.05106 (16)	0.0210 (5)
C3	0.4690 (3)	0.07967 (10)	−0.00795 (17)	0.0230 (5)
C4	0.3932 (3)	0.09152 (10)	−0.11067 (17)	0.0218 (5)
C5	0.2261 (3)	0.07064 (10)	−0.14871 (17)	0.0227 (5)
H5A	0.1707	0.0971	−0.1986	0.027*
H5B	0.2296	0.0329	−0.1785	0.027*
C6	0.4445 (3)	0.04187 (10)	0.14446 (17)	0.0226 (5)
H6	0.5488	0.0566	0.1639	0.027*
C7	0.3796 (3)	0.01625 (10)	0.22028 (17)	0.0229 (5)
C8	0.4273 (3)	0.03902 (11)	0.31209 (18)	0.0278 (5)
H8	0.5014	0.0694	0.3232	0.033*
C9	0.3683 (3)	0.01808 (11)	0.38682 (18)	0.0287 (5)
H9	0.3993	0.0348	0.4483	0.034*
C10	0.2636 (3)	−0.02744 (10)	0.37199 (18)	0.0260 (5)
C11	0.2186 (3)	−0.05167 (10)	0.28188 (17)	0.0253 (5)
H11	0.1489	−0.0834	0.2720	0.030*
C12	0.2746 (3)	−0.02990 (10)	0.20634 (17)	0.0234 (5)
H12	0.2418	−0.0463	0.1448	0.028*
C13	0.2037 (3)	−0.05211 (11)	0.45243 (19)	0.0332 (6)
C14	0.4793 (3)	0.12141 (10)	−0.16082 (17)	0.0238 (5)
H14	0.5802	0.1337	−0.1262	0.029*
C15	0.4379 (3)	0.13748 (10)	−0.26189 (17)	0.0254 (5)
C16	0.5050 (3)	0.18706 (12)	−0.28977 (19)	0.0351 (6)
H16	0.5766	0.2086	−0.2434	0.042*
C17	0.4692 (4)	0.20519 (12)	−0.3833 (2)	0.0391 (7)
H17	0.5156	0.2389	−0.4010	0.047*
C18	0.3644 (3)	0.17365 (11)	−0.45169 (18)	0.0308 (6)
C19	0.3013 (3)	0.12340 (10)	−0.42675 (18)	0.0278 (5)
H19	0.2331	0.1013	−0.4740	0.033*
C20	0.3378 (3)	0.10541 (10)	−0.33248 (17)	0.0253 (5)
H20	0.2943	0.0708	−0.3157	0.030*
C21	0.3248 (4)	0.19397 (14)	−0.5530 (2)	0.0449 (7)
C22	0.1810 (3)	0.17179 (9)	0.01432 (16)	0.0209 (5)
C23	0.2330 (3)	0.16704 (10)	0.11316 (17)	0.0228 (5)
H23	0.1926	0.1380	0.1470	0.027*
C24	0.3443 (3)	0.20520 (10)	0.16107 (17)	0.0257 (5)
H24	0.3798	0.2022	0.2283	0.031*
C25	0.4053 (3)	0.24791 (10)	0.11270 (19)	0.0291 (6)
C26	0.3515 (3)	0.25165 (10)	0.01411 (19)	0.0312 (6)
H26	0.3920	0.2807	−0.0197	0.037*
C27	0.2402 (3)	0.21396 (10)	−0.03562 (17)	0.0263 (5)
H27	0.2049	0.2169	−0.1029	0.032*
C28	0.5273 (4)	0.28894 (13)	0.1653 (2)	0.0435 (7)
H28A	0.5058	0.2972	0.2280	0.065*
H28B	0.5227	0.3243	0.1287	0.065*
H28C	0.6328	0.2721	0.1736	0.065*
C29	0.8703 (3)	0.13523 (12)	0.2147 (2)	0.0350 (6)
H29A	0.8038	0.1310	0.1495	0.042*
H29B	0.9529	0.1639	0.2124	0.042*
Cl1	0.96073 (11)	0.06994 (3)	0.25227 (7)	0.0580 (2)
Cl2	0.75207 (10)	0.15934 (4)	0.29150 (6)	0.0525 (2)
F1	0.2185 (2)	−0.01731 (8)	0.52703 (12)	0.0533 (5)
F2	0.0510 (2)	−0.06637 (10)	0.42708 (13)	0.0611 (6)
F3	0.2815 (3)	−0.09948 (8)	0.48702 (14)	0.0662 (6)
F4	0.193 (3)	0.1743 (11)	−0.6004 (16)	0.106 (7)	0.51 (3)
F5	0.4359 (17)	0.1789 (8)	−0.5972 (8)	0.107 (4)	0.51 (3)
F6	0.3157 (16)	0.2480 (4)	−0.5636 (7)	0.064 (3)	0.51 (3)
F4'	0.255 (4)	0.2452 (7)	−0.5575 (10)	0.127 (6)	0.49 (3)
F5'	0.226 (3)	0.1614 (10)	−0.6123 (15)	0.087 (6)	0.49 (3)
F6'	0.4461 (11)	0.1994 (9)	−0.5910 (7)	0.114 (6)	0.49 (3)
N1	0.1363 (2)	0.06618 (8)	−0.07383 (13)	0.0197 (4)
O2	−0.0492 (2)	0.10275 (8)	0.01773 (13)	0.0325 (4)
O3	−0.0339 (2)	0.14734 (7)	−0.13659 (13)	0.0317 (4)
S1	0.04238 (7)	0.12239 (2)	−0.04711 (4)	0.02246 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0214 (9)	0.0512 (12)	0.0287 (10)	−0.0091 (8)	0.0025 (8)	0.0042 (8)
C1	0.0196 (11)	0.0220 (11)	0.0243 (12)	−0.0020 (9)	0.0021 (9)	0.0036 (9)
C2	0.0206 (11)	0.0186 (11)	0.0233 (12)	0.0011 (9)	0.0038 (9)	−0.0001 (9)
C3	0.0195 (12)	0.0255 (12)	0.0246 (13)	0.0025 (9)	0.0061 (10)	−0.0029 (9)
C4	0.0199 (11)	0.0233 (11)	0.0223 (12)	0.0017 (9)	0.0049 (9)	−0.0017 (9)
C5	0.0218 (12)	0.0267 (12)	0.0200 (12)	−0.0014 (9)	0.0053 (9)	−0.0037 (9)
C6	0.0200 (11)	0.0214 (11)	0.0264 (13)	−0.0006 (9)	0.0048 (10)	−0.0001 (9)
C7	0.0208 (11)	0.0234 (12)	0.0236 (13)	0.0020 (9)	0.0032 (10)	0.0031 (9)
C8	0.0271 (13)	0.0273 (12)	0.0272 (13)	−0.0062 (10)	0.0024 (10)	−0.0008 (10)
C9	0.0323 (14)	0.0314 (13)	0.0223 (13)	−0.0063 (11)	0.0056 (11)	−0.0041 (10)
C10	0.0242 (12)	0.0274 (12)	0.0259 (13)	0.0007 (10)	0.0049 (10)	0.0022 (10)
C11	0.0237 (12)	0.0236 (12)	0.0270 (13)	−0.0010 (10)	0.0027 (10)	0.0007 (10)
C12	0.0226 (12)	0.0246 (12)	0.0214 (12)	0.0024 (9)	0.0017 (9)	−0.0003 (9)
C13	0.0334 (14)	0.0363 (15)	0.0304 (14)	−0.0065 (12)	0.0083 (12)	−0.0015 (11)
C14	0.0203 (11)	0.0254 (12)	0.0247 (13)	0.0003 (9)	0.0030 (10)	−0.0016 (10)
C15	0.0238 (12)	0.0291 (13)	0.0247 (13)	−0.0010 (10)	0.0082 (10)	0.0014 (10)
C16	0.0389 (15)	0.0356 (14)	0.0299 (14)	−0.0155 (12)	0.0056 (12)	−0.0001 (11)
C17	0.0461 (17)	0.0375 (15)	0.0332 (15)	−0.0174 (13)	0.0081 (13)	0.0055 (12)
C18	0.0353 (14)	0.0339 (14)	0.0239 (13)	−0.0066 (11)	0.0085 (11)	0.0036 (11)
C19	0.0326 (13)	0.0267 (12)	0.0253 (13)	−0.0053 (11)	0.0092 (11)	−0.0030 (10)
C20	0.0287 (13)	0.0211 (11)	0.0279 (13)	−0.0028 (10)	0.0101 (10)	−0.0020 (10)
C21	0.054 (2)	0.0446 (18)	0.0345 (16)	−0.0121 (15)	0.0066 (15)	0.0090 (14)
C22	0.0201 (11)	0.0204 (11)	0.0213 (12)	0.0020 (9)	0.0031 (9)	−0.0038 (9)
C23	0.0252 (12)	0.0220 (11)	0.0220 (12)	0.0018 (9)	0.0068 (10)	0.0008 (9)
C24	0.0276 (13)	0.0301 (13)	0.0182 (12)	0.0032 (10)	0.0027 (10)	−0.0028 (10)
C25	0.0314 (13)	0.0257 (12)	0.0291 (14)	−0.0028 (10)	0.0042 (11)	−0.0059 (10)
C26	0.0393 (15)	0.0245 (12)	0.0304 (14)	−0.0080 (11)	0.0089 (12)	0.0011 (10)
C27	0.0336 (14)	0.0240 (12)	0.0196 (12)	−0.0018 (10)	0.0025 (10)	0.0004 (9)
C28	0.0471 (18)	0.0382 (16)	0.0407 (17)	−0.0171 (13)	0.0006 (14)	−0.0076 (13)
C29	0.0333 (14)	0.0382 (15)	0.0343 (15)	0.0004 (12)	0.0092 (12)	−0.0020 (12)
Cl1	0.0552 (5)	0.0386 (4)	0.0731 (6)	0.0080 (4)	−0.0008 (4)	−0.0017 (4)
Cl2	0.0503 (5)	0.0603 (5)	0.0525 (5)	−0.0012 (4)	0.0233 (4)	−0.0152 (4)
F1	0.0740 (13)	0.0572 (11)	0.0358 (10)	−0.0242 (10)	0.0276 (9)	−0.0126 (8)
F2	0.0443 (11)	0.0990 (16)	0.0428 (11)	−0.0341 (10)	0.0158 (9)	−0.0047 (10)
F3	0.0966 (16)	0.0520 (11)	0.0606 (13)	0.0175 (11)	0.0397 (12)	0.0311 (10)
F4	0.091 (7)	0.149 (16)	0.050 (9)	−0.078 (10)	−0.043 (7)	0.053 (8)
F5	0.137 (10)	0.161 (8)	0.040 (4)	0.075 (8)	0.054 (6)	0.035 (4)
F6	0.111 (6)	0.034 (3)	0.037 (4)	−0.020 (4)	−0.006 (4)	0.016 (2)
F4'	0.207 (15)	0.112 (10)	0.070 (5)	0.076 (9)	0.045 (8)	0.053 (6)
F5'	0.138 (17)	0.077 (5)	0.030 (3)	−0.065 (7)	−0.018 (6)	0.008 (3)
F6'	0.062 (5)	0.245 (14)	0.030 (4)	−0.085 (9)	−0.002 (4)	0.032 (6)
N1	0.0176 (9)	0.0213 (10)	0.0196 (10)	−0.0010 (7)	0.0028 (8)	0.0006 (8)
O2	0.0223 (9)	0.0379 (10)	0.0407 (11)	−0.0069 (8)	0.0143 (8)	−0.0092 (8)
O3	0.0296 (10)	0.0300 (9)	0.0290 (10)	0.0046 (7)	−0.0074 (8)	−0.0020 (8)
S1	0.0173 (3)	0.0243 (3)	0.0244 (3)	0.0002 (2)	0.0017 (2)	−0.0038 (2)

Geometric parameters (Å, º) top

O1—C3	1.225 (3)	C17—C18	1.394 (4)
C1—N1	1.475 (3)	C17—H17	0.9500
C1—C2	1.511 (3)	C18—C19	1.383 (3)
C1—H1A	0.9900	C18—C21	1.499 (4)
C1—H1B	0.9900	C19—C20	1.388 (3)
C2—C6	1.347 (3)	C19—H19	0.9500
C2—C3	1.494 (3)	C20—H20	0.9500
C3—C4	1.503 (3)	C21—F6	1.279 (10)
C4—C14	1.347 (3)	C21—F4	1.279 (19)
C4—C5	1.512 (3)	C21—F6'	1.296 (10)
C5—N1	1.468 (3)	C21—F5'	1.311 (18)
C5—H5A	0.9900	C21—F5	1.317 (9)
C5—H5B	0.9900	C21—F4'	1.342 (16)
C6—C7	1.465 (3)	C22—C27	1.389 (3)
C6—H6	0.9500	C22—C23	1.397 (3)
C7—C8	1.399 (3)	C22—S1	1.760 (2)
C7—C12	1.401 (3)	C23—C24	1.383 (3)
C8—C9	1.381 (3)	C23—H23	0.9500
C8—H8	0.9500	C24—C25	1.392 (4)
C9—C10	1.388 (3)	C24—H24	0.9500
C9—H9	0.9500	C25—C26	1.394 (4)
C10—C11	1.390 (3)	C25—C28	1.505 (4)
C10—C13	1.489 (4)	C26—C27	1.385 (3)
C11—C12	1.385 (3)	C26—H26	0.9500
C11—H11	0.9500	C27—H27	0.9500
C12—H12	0.9500	C28—H28A	0.9800
C13—F1	1.333 (3)	C28—H28B	0.9800
C13—F2	1.335 (3)	C28—H28C	0.9800
C13—F3	1.339 (3)	C29—Cl1	1.753 (3)
C14—C15	1.467 (3)	C29—Cl2	1.761 (3)
C14—H14	0.9500	C29—H29A	0.9900
C15—C20	1.399 (3)	C29—H29B	0.9900
C15—C16	1.401 (4)	N1—S1	1.6428 (19)
C16—C17	1.380 (4)	O2—S1	1.4309 (18)
C16—H16	0.9500	O3—S1	1.4346 (18)

N1—C1—C2	111.56 (18)	C19—C18—C17	120.3 (2)
N1—C1—H1A	109.3	C19—C18—C21	120.5 (2)
C2—C1—H1A	109.3	C17—C18—C21	119.2 (2)
N1—C1—H1B	109.3	C18—C19—C20	119.8 (2)
C2—C1—H1B	109.3	C18—C19—H19	120.1
H1A—C1—H1B	108.0	C20—C19—H19	120.1
C6—C2—C3	116.7 (2)	C19—C20—C15	120.9 (2)
C6—C2—C1	124.7 (2)	C19—C20—H20	119.5
C3—C2—C1	118.4 (2)	C15—C20—H20	119.5
O1—C3—C2	120.9 (2)	F6—C21—F4	105.8 (12)
O1—C3—C4	120.3 (2)	F6'—C21—F5'	104.9 (14)
C2—C3—C4	118.8 (2)	F6—C21—F5	104.0 (8)
C14—C4—C3	116.8 (2)	F4—C21—F5	107.9 (13)
C14—C4—C5	125.2 (2)	F6'—C21—F4'	106.8 (9)
C3—C4—C5	117.9 (2)	F5'—C21—F4'	105.7 (14)
N1—C5—C4	112.36 (19)	F6—C21—C18	115.3 (5)
N1—C5—H5A	109.1	F4—C21—C18	112.7 (11)
C4—C5—H5A	109.1	F6'—C21—C18	114.3 (6)
N1—C5—H5B	109.1	F5'—C21—C18	114.9 (11)
C4—C5—H5B	109.1	F5—C21—C18	110.6 (5)
H5A—C5—H5B	107.9	F4'—C21—C18	109.6 (7)
C2—C6—C7	129.1 (2)	C27—C22—C23	120.8 (2)
C2—C6—H6	115.4	C27—C22—S1	120.07 (18)
C7—C6—H6	115.4	C23—C22—S1	119.13 (18)
C8—C7—C12	118.4 (2)	C24—C23—C22	119.1 (2)
C8—C7—C6	117.7 (2)	C24—C23—H23	120.5
C12—C7—C6	123.9 (2)	C22—C23—H23	120.5
C9—C8—C7	121.1 (2)	C23—C24—C25	121.3 (2)
C9—C8—H8	119.4	C23—C24—H24	119.4
C7—C8—H8	119.4	C25—C24—H24	119.4
C8—C9—C10	119.9 (2)	C24—C25—C26	118.5 (2)
C8—C9—H9	120.0	C24—C25—C28	120.9 (2)
C10—C9—H9	120.0	C26—C25—C28	120.6 (2)
C9—C10—C11	119.8 (2)	C27—C26—C25	121.4 (2)
C9—C10—C13	120.7 (2)	C27—C26—H26	119.3
C11—C10—C13	119.5 (2)	C25—C26—H26	119.3
C12—C11—C10	120.4 (2)	C26—C27—C22	119.0 (2)
C12—C11—H11	119.8	C26—C27—H27	120.5
C10—C11—H11	119.8	C22—C27—H27	120.5
C11—C12—C7	120.3 (2)	C25—C28—H28A	109.5
C11—C12—H12	119.8	C25—C28—H28B	109.5
C7—C12—H12	119.8	H28A—C28—H28B	109.5
F1—C13—F2	106.5 (2)	C25—C28—H28C	109.5
F1—C13—F3	105.2 (2)	H28A—C28—H28C	109.5
F2—C13—F3	106.2 (2)	H28B—C28—H28C	109.5
F1—C13—C10	113.6 (2)	Cl1—C29—Cl2	111.82 (16)
F2—C13—C10	112.5 (2)	Cl1—C29—H29A	109.3
F3—C13—C10	112.3 (2)	Cl2—C29—H29A	109.3
C4—C14—C15	128.6 (2)	Cl1—C29—H29B	109.3
C4—C14—H14	115.7	Cl2—C29—H29B	109.3
C15—C14—H14	115.7	H29A—C29—H29B	107.9
C20—C15—C16	118.0 (2)	C5—N1—C1	112.70 (18)
C20—C15—C14	123.7 (2)	C5—N1—S1	119.13 (15)
C16—C15—C14	118.2 (2)	C1—N1—S1	118.11 (15)
C17—C16—C15	121.3 (2)	O2—S1—O3	120.40 (11)
C17—C16—H16	119.4	O2—S1—N1	105.67 (10)
C15—C16—H16	119.4	O3—S1—N1	105.75 (10)
C16—C17—C18	119.6 (2)	O2—S1—C22	107.56 (11)
C16—C17—H17	120.2	O3—S1—C22	107.85 (11)
C18—C17—H17	120.2	N1—S1—C22	109.25 (10)

N1—C1—C2—C6	145.7 (2)	C21—C18—C19—C20	−179.4 (3)
N1—C1—C2—C3	−29.1 (3)	C18—C19—C20—C15	0.1 (4)
C6—C2—C3—O1	5.9 (3)	C16—C15—C20—C19	−2.5 (4)
C1—C2—C3—O1	−178.8 (2)	C14—C15—C20—C19	179.0 (2)
C6—C2—C3—C4	−174.8 (2)	C19—C18—C21—F6	145.8 (7)
C1—C2—C3—C4	0.5 (3)	C17—C18—C21—F6	−35.9 (8)
O1—C3—C4—C14	−1.7 (3)	C19—C18—C21—F4	24.3 (17)
C2—C3—C4—C14	179.0 (2)	C17—C18—C21—F4	−157.5 (17)
O1—C3—C4—C5	180.0 (2)	C19—C18—C21—F6'	−119.9 (11)
C2—C3—C4—C5	0.6 (3)	C17—C18—C21—F6'	58.3 (11)
C14—C4—C5—N1	−150.9 (2)	C19—C18—C21—F5'	1.5 (14)
C3—C4—C5—N1	27.2 (3)	C17—C18—C21—F5'	179.7 (14)
C3—C2—C6—C7	175.6 (2)	C19—C18—C21—F5	−96.6 (11)
C1—C2—C6—C7	0.7 (4)	C17—C18—C21—F5	81.7 (11)
C2—C6—C7—C8	−147.9 (3)	C19—C18—C21—F4'	120.2 (15)
C2—C6—C7—C12	32.9 (4)	C17—C18—C21—F4'	−61.6 (15)
C12—C7—C8—C9	−2.4 (4)	C27—C22—C23—C24	0.3 (3)
C6—C7—C8—C9	178.4 (2)	S1—C22—C23—C24	178.72 (18)
C7—C8—C9—C10	2.0 (4)	C22—C23—C24—C25	−0.2 (4)
C8—C9—C10—C11	−0.1 (4)	C23—C24—C25—C26	0.1 (4)
C8—C9—C10—C13	177.5 (2)	C23—C24—C25—C28	−179.5 (2)
C9—C10—C11—C12	−1.5 (4)	C24—C25—C26—C27	−0.1 (4)
C13—C10—C11—C12	−179.1 (2)	C28—C25—C26—C27	179.5 (3)
C10—C11—C12—C7	1.1 (4)	C25—C26—C27—C22	0.3 (4)
C8—C7—C12—C11	0.8 (3)	C23—C22—C27—C26	−0.3 (4)
C6—C7—C12—C11	−180.0 (2)	S1—C22—C27—C26	−178.74 (19)
C9—C10—C13—F1	19.5 (4)	C4—C5—N1—C1	−58.1 (2)
C11—C10—C13—F1	−162.9 (2)	C4—C5—N1—S1	86.8 (2)
C9—C10—C13—F2	140.7 (3)	C2—C1—N1—C5	58.9 (2)
C11—C10—C13—F2	−41.7 (3)	C2—C1—N1—S1	−86.3 (2)
C9—C10—C13—F3	−99.6 (3)	C5—N1—S1—O2	172.46 (16)
C11—C10—C13—F3	78.0 (3)	C1—N1—S1—O2	−44.55 (18)
C3—C4—C14—C15	177.9 (2)	C5—N1—S1—O3	43.76 (19)
C5—C4—C14—C15	−3.9 (4)	C1—N1—S1—O3	−173.25 (16)
C4—C14—C15—C20	−29.5 (4)	C5—N1—S1—C22	−72.08 (18)
C4—C14—C15—C16	152.1 (3)	C1—N1—S1—C22	70.91 (18)
C20—C15—C16—C17	2.5 (4)	C27—C22—S1—O2	−153.82 (19)
C14—C15—C16—C17	−178.9 (3)	C23—C22—S1—O2	27.7 (2)
C15—C16—C17—C18	−0.1 (5)	C27—C22—S1—O3	−22.6 (2)
C16—C17—C18—C19	−2.4 (4)	C23—C22—S1—O3	159.00 (18)
C16—C17—C18—C21	179.4 (3)	C27—C22—S1—N1	91.9 (2)
C17—C18—C19—C20	2.4 (4)	C23—C22—S1—N1	−86.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1ⁱ	0.99	2.53	3.390 (3)	145
C1—H1A···O2ⁱⁱ	0.99	2.61	3.365 (3)	133
C5—H5B···Cl1ⁱ	0.99	2.98	3.832 (2)	144
C29—H29A···O1	0.99	2.34	3.279 (3)	159
C29—H29A···O2ⁱⁱⁱ	0.99	2.60	3.162 (3)	116

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

(3E,5E)-1-(4-Fluorobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one (5) top

Crystal data top

C₂₇H₁₈F₇NO₃S	Z = 2
M_r = 569.48	F(000) = 580
Triclinic, P1	D_x = 1.551 Mg m⁻³
a = 8.5664 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0932 (8) Å	Cell parameters from 4723 reflections
c = 14.3871 (12) Å	θ = 2.4–26.3°
α = 90.590 (4)°	µ = 0.22 mm⁻¹
β = 98.592 (4)°	T = 150 K
γ = 97.309 (4)°	Block, yellow
V = 1219.44 (17) Å³	0.26 × 0.17 × 0.10 mm

Data collection top

Bruker SMART CCD area detector diffractometer	R_int = 0.074
Radiation source: sealed tube	θ_max = 26.0°, θ_min = 2.4°
phi and ω scans	h = −10→10
21256 measured reflections	k = −12→12
4790 independent reflections	l = −17→17
3187 reflections with I > 2σ(I)

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0558P)² + 0.8089P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
4790 reflections	Δρ_max = 0.48 e Å⁻³
380 parameters	Δρ_min = −0.38 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.2745 (3)	0.4646 (3)	0.09345 (19)	0.0266 (6)
H1A	0.2746	0.4750	0.1620	0.032*
H1B	0.2856	0.5549	0.0671	0.032*
C2	0.4151 (3)	0.3950 (3)	0.07680 (18)	0.0229 (6)
C3	0.3998 (3)	0.3125 (3)	−0.01181 (18)	0.0235 (6)
C4	0.2444 (3)	0.2949 (3)	−0.07648 (18)	0.0233 (6)
C5	0.1130 (3)	0.3682 (3)	−0.05191 (18)	0.0278 (6)
H5A	0.1188	0.4558	−0.0823	0.033*
H5B	0.0089	0.3163	−0.0770	0.033*
C6	0.5502 (3)	0.3970 (3)	0.13772 (18)	0.0252 (6)
H6	0.6278	0.3489	0.1172	0.030*
C7	0.5962 (3)	0.4619 (3)	0.23108 (18)	0.0231 (6)
C8	0.7029 (3)	0.4042 (3)	0.2959 (2)	0.0277 (6)
H8	0.7437	0.3262	0.2778	0.033*
C9	0.7510 (3)	0.4579 (3)	0.3861 (2)	0.0294 (6)
H9	0.8232	0.4168	0.4296	0.035*
C10	0.6926 (3)	0.5725 (3)	0.41233 (19)	0.0260 (6)
C11	0.5903 (3)	0.6343 (3)	0.34794 (19)	0.0271 (6)
H11	0.5529	0.7141	0.3656	0.032*
C12	0.5429 (3)	0.5799 (3)	0.25799 (19)	0.0249 (6)
H12	0.4735	0.6231	0.2140	0.030*
C13	0.7432 (4)	0.6305 (3)	0.5094 (2)	0.0331 (7)
C14	0.2319 (3)	0.2154 (3)	−0.15292 (19)	0.0252 (6)
H14	0.3198	0.1678	−0.1564	0.030*
C15	0.1018 (3)	0.1914 (3)	−0.23187 (18)	0.0254 (6)
C16	0.0801 (3)	0.0706 (3)	−0.2831 (2)	0.0328 (7)
H16	0.1465	0.0043	−0.2639	0.039*
C17	−0.0355 (3)	0.0453 (3)	−0.3610 (2)	0.0361 (7)
H17	−0.0490	−0.0380	−0.3945	0.043*
C18	−0.1322 (3)	0.1420 (3)	−0.3901 (2)	0.0316 (7)
C19	−0.1114 (4)	0.2635 (3)	−0.3416 (2)	0.0349 (7)
H19	−0.1765	0.3303	−0.3621	0.042*
C20	0.0040 (3)	0.2877 (3)	−0.26338 (19)	0.0298 (6)
H20	0.0173	0.3714	−0.2303	0.036*
C21	−0.2521 (4)	0.1177 (4)	−0.4773 (2)	0.0420 (8)
C22	0.1738 (3)	0.1683 (3)	0.15526 (18)	0.0225 (6)
C23	0.2648 (3)	0.1949 (3)	0.24334 (19)	0.0277 (6)
H23	0.2506	0.2695	0.2805	0.033*
C24	0.3765 (3)	0.1122 (3)	0.2766 (2)	0.0318 (7)
H24	0.4408	0.1290	0.3363	0.038*
C25	0.3913 (3)	0.0050 (3)	0.2207 (2)	0.0324 (7)
C26	0.3034 (3)	−0.0243 (3)	0.1338 (2)	0.0332 (7)
H26	0.3173	−0.1000	0.0976	0.040*
C27	0.1933 (3)	0.0600 (3)	0.1001 (2)	0.0283 (6)
H27	0.1315	0.0436	0.0396	0.034*
F1	0.6329 (10)	0.6923 (9)	0.5414 (5)	0.061 (3)	0.542 (19)
F2	0.763 (2)	0.5383 (5)	0.5743 (3)	0.077 (4)	0.542 (19)
F3	0.8690 (9)	0.7143 (13)	0.5196 (5)	0.076 (4)	0.542 (19)
F3'	0.8703 (14)	0.5860 (14)	0.5537 (7)	0.079 (5)	0.458 (19)
F2'	0.6354 (14)	0.613 (2)	0.5590 (7)	0.119 (8)	0.458 (19)
F1'	0.783 (3)	0.7594 (7)	0.5101 (6)	0.096 (6)	0.458 (19)
F4	−0.3734 (2)	0.1880 (3)	−0.47810 (15)	0.0800 (8)
F5	−0.3093 (3)	−0.0095 (2)	−0.49351 (16)	0.0797 (8)
F6	−0.1910 (2)	0.1550 (2)	−0.55509 (12)	0.0499 (5)
F7	0.4980 (2)	−0.0776 (2)	0.25495 (13)	0.0534 (5)
N1	0.1225 (2)	0.3894 (2)	0.04994 (15)	0.0243 (5)
O1	0.5140 (2)	0.26338 (19)	−0.03256 (13)	0.0310 (5)
O2	0.0046 (2)	0.3482 (2)	0.19369 (14)	0.0369 (5)
O3	−0.0936 (2)	0.2044 (2)	0.05130 (15)	0.0384 (5)
S1	0.03566 (8)	0.27738 (7)	0.11325 (5)	0.02732 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0285 (14)	0.0253 (15)	0.0277 (15)	0.0074 (12)	0.0068 (12)	−0.0020 (12)
C2	0.0271 (14)	0.0199 (14)	0.0241 (14)	0.0063 (11)	0.0093 (11)	0.0023 (11)
C3	0.0266 (14)	0.0219 (14)	0.0242 (14)	0.0067 (11)	0.0075 (11)	0.0031 (11)
C4	0.0254 (14)	0.0235 (14)	0.0236 (14)	0.0083 (11)	0.0081 (11)	0.0038 (11)
C5	0.0301 (15)	0.0319 (16)	0.0235 (14)	0.0126 (12)	0.0038 (12)	−0.0006 (12)
C6	0.0267 (14)	0.0237 (15)	0.0281 (15)	0.0076 (11)	0.0101 (12)	0.0014 (11)
C7	0.0229 (13)	0.0238 (14)	0.0240 (14)	0.0034 (11)	0.0075 (11)	0.0031 (11)
C8	0.0280 (14)	0.0242 (15)	0.0329 (16)	0.0068 (12)	0.0081 (12)	0.0005 (12)
C9	0.0286 (15)	0.0306 (16)	0.0289 (16)	0.0066 (12)	0.0016 (12)	0.0035 (12)
C10	0.0256 (14)	0.0265 (15)	0.0256 (15)	0.0006 (12)	0.0056 (12)	0.0027 (12)
C11	0.0310 (15)	0.0236 (15)	0.0280 (15)	0.0062 (12)	0.0066 (12)	0.0002 (12)
C12	0.0271 (14)	0.0223 (14)	0.0251 (15)	0.0042 (11)	0.0028 (11)	0.0021 (11)
C13	0.0379 (17)	0.0293 (17)	0.0307 (16)	0.0036 (14)	0.0008 (14)	−0.0011 (13)
C14	0.0229 (13)	0.0248 (15)	0.0296 (15)	0.0049 (11)	0.0080 (11)	0.0011 (12)
C15	0.0251 (14)	0.0283 (15)	0.0238 (14)	0.0006 (12)	0.0091 (11)	0.0004 (12)
C16	0.0265 (14)	0.0358 (17)	0.0362 (17)	0.0043 (13)	0.0056 (13)	−0.0052 (14)
C17	0.0311 (16)	0.0358 (18)	0.0403 (18)	−0.0006 (13)	0.0065 (14)	−0.0104 (14)
C18	0.0250 (14)	0.0378 (18)	0.0307 (16)	−0.0044 (13)	0.0068 (12)	0.0026 (13)
C19	0.0368 (17)	0.0368 (18)	0.0317 (17)	0.0074 (14)	0.0049 (14)	0.0088 (14)
C20	0.0361 (16)	0.0278 (15)	0.0257 (15)	0.0034 (13)	0.0062 (13)	0.0016 (12)
C21	0.0342 (17)	0.049 (2)	0.0399 (19)	−0.0007 (15)	0.0025 (15)	−0.0023 (16)
C22	0.0219 (13)	0.0216 (14)	0.0252 (14)	0.0042 (11)	0.0063 (11)	0.0030 (11)
C23	0.0332 (15)	0.0277 (15)	0.0234 (15)	0.0067 (12)	0.0059 (12)	0.0005 (12)
C24	0.0353 (16)	0.0363 (17)	0.0243 (15)	0.0083 (13)	0.0024 (12)	0.0058 (13)
C25	0.0302 (15)	0.0339 (17)	0.0368 (17)	0.0148 (13)	0.0078 (13)	0.0082 (13)
C26	0.0397 (17)	0.0276 (16)	0.0351 (17)	0.0115 (13)	0.0091 (14)	−0.0018 (13)
C27	0.0298 (15)	0.0265 (15)	0.0287 (15)	0.0048 (12)	0.0042 (12)	−0.0023 (12)
F1	0.065 (5)	0.091 (6)	0.031 (3)	0.043 (5)	−0.002 (3)	−0.022 (3)
F2	0.162 (12)	0.037 (3)	0.026 (2)	0.024 (4)	−0.011 (4)	0.0051 (18)
F3	0.061 (4)	0.104 (10)	0.052 (4)	−0.047 (4)	0.019 (3)	−0.036 (5)
F3'	0.081 (6)	0.095 (9)	0.055 (5)	0.055 (6)	−0.044 (4)	−0.033 (5)
F2'	0.069 (8)	0.23 (2)	0.041 (5)	−0.071 (10)	0.033 (5)	−0.045 (9)
F1'	0.186 (16)	0.032 (3)	0.050 (4)	−0.012 (5)	−0.029 (7)	−0.008 (3)
F4	0.0400 (12)	0.141 (2)	0.0594 (14)	0.0360 (13)	−0.0095 (10)	−0.0291 (15)
F5	0.0899 (17)	0.0570 (15)	0.0673 (15)	−0.0307 (13)	−0.0355 (13)	0.0098 (12)
F6	0.0537 (12)	0.0604 (13)	0.0344 (11)	0.0093 (10)	0.0014 (9)	0.0023 (9)
F7	0.0586 (12)	0.0606 (13)	0.0484 (12)	0.0399 (10)	0.0041 (9)	0.0096 (10)
N1	0.0237 (11)	0.0269 (13)	0.0245 (12)	0.0085 (10)	0.0061 (9)	−0.0005 (10)
O1	0.0285 (10)	0.0352 (11)	0.0319 (11)	0.0138 (9)	0.0060 (8)	−0.0062 (9)
O2	0.0414 (12)	0.0437 (13)	0.0338 (12)	0.0190 (10)	0.0206 (9)	0.0030 (10)
O3	0.0212 (10)	0.0460 (13)	0.0455 (13)	0.0031 (9)	−0.0021 (9)	0.0019 (10)
S1	0.0225 (3)	0.0323 (4)	0.0300 (4)	0.0100 (3)	0.0079 (3)	0.0017 (3)

Geometric parameters (Å, º) top

C1—N1	1.469 (3)	C14—C15	1.462 (4)
C1—C2	1.516 (3)	C14—H14	0.9500
C1—H1A	0.9900	C15—C16	1.396 (4)
C1—H1B	0.9900	C15—C20	1.398 (4)
C2—C6	1.341 (4)	C16—C17	1.378 (4)
C2—C3	1.495 (4)	C16—H16	0.9500
C3—O1	1.225 (3)	C17—C18	1.388 (4)
C3—C4	1.495 (4)	C17—H17	0.9500
C4—C14	1.338 (4)	C18—C19	1.383 (4)
C4—C5	1.505 (3)	C18—C21	1.494 (4)
C5—N1	1.467 (3)	C19—C20	1.380 (4)
C5—H5A	0.9900	C19—H19	0.9500
C5—H5B	0.9900	C20—H20	0.9500
C6—C7	1.465 (4)	C21—F5	1.320 (4)
C6—H6	0.9500	C21—F4	1.330 (4)
C7—C8	1.391 (4)	C21—F6	1.343 (4)
C7—C12	1.400 (4)	C22—C27	1.386 (4)
C8—C9	1.384 (4)	C22—C23	1.390 (4)
C8—H8	0.9500	C22—S1	1.763 (2)
C9—C10	1.387 (4)	C23—C24	1.384 (4)
C9—H9	0.9500	C23—H23	0.9500
C10—C11	1.387 (4)	C24—C25	1.372 (4)
C10—C13	1.489 (4)	C24—H24	0.9500
C11—C12	1.383 (4)	C25—F7	1.357 (3)
C11—H11	0.9500	C25—C26	1.368 (4)
C12—H12	0.9500	C26—C27	1.387 (4)
C13—F2'	1.246 (9)	C26—H26	0.9500
C13—F3	1.272 (7)	C27—H27	0.9500
C13—F1'	1.303 (8)	N1—S1	1.634 (2)
C13—F3'	1.310 (6)	O2—S1	1.430 (2)
C13—F1	1.331 (7)	O3—S1	1.431 (2)
C13—F2	1.333 (5)

N1—C1—C2	111.8 (2)	C4—C14—C15	129.0 (2)
N1—C1—H1A	109.3	C4—C14—H14	115.5
C2—C1—H1A	109.3	C15—C14—H14	115.5
N1—C1—H1B	109.3	C16—C15—C20	117.6 (3)
C2—C1—H1B	109.3	C16—C15—C14	119.0 (2)
H1A—C1—H1B	107.9	C20—C15—C14	123.2 (3)
C6—C2—C3	117.2 (2)	C17—C16—C15	121.5 (3)
C6—C2—C1	124.8 (2)	C17—C16—H16	119.2
C3—C2—C1	117.9 (2)	C15—C16—H16	119.2
O1—C3—C4	120.4 (2)	C16—C17—C18	119.6 (3)
O1—C3—C2	120.6 (2)	C16—C17—H17	120.2
C4—C3—C2	119.0 (2)	C18—C17—H17	120.2
C14—C4—C3	117.6 (2)	C19—C18—C17	120.0 (3)
C14—C4—C5	124.3 (2)	C19—C18—C21	120.1 (3)
C3—C4—C5	118.1 (2)	C17—C18—C21	119.8 (3)
N1—C5—C4	112.3 (2)	C20—C19—C18	119.9 (3)
N1—C5—H5A	109.1	C20—C19—H19	120.0
C4—C5—H5A	109.1	C18—C19—H19	120.0
N1—C5—H5B	109.1	C19—C20—C15	121.2 (3)
C4—C5—H5B	109.1	C19—C20—H20	119.4
H5A—C5—H5B	107.9	C15—C20—H20	119.4
C2—C6—C7	129.8 (2)	F5—C21—F4	108.6 (3)
C2—C6—H6	115.1	F5—C21—F6	104.6 (3)
C7—C6—H6	115.1	F4—C21—F6	103.8 (3)
C8—C7—C12	118.2 (2)	F5—C21—C18	113.4 (3)
C8—C7—C6	117.7 (2)	F4—C21—C18	113.2 (3)
C12—C7—C6	124.1 (2)	F6—C21—C18	112.5 (3)
C9—C8—C7	121.5 (2)	C27—C22—C23	120.9 (2)
C9—C8—H8	119.3	C27—C22—S1	120.3 (2)
C7—C8—H8	119.3	C23—C22—S1	118.8 (2)
C8—C9—C10	119.3 (2)	C24—C23—C22	119.7 (3)
C8—C9—H9	120.3	C24—C23—H23	120.2
C10—C9—H9	120.3	C22—C23—H23	120.2
C11—C10—C9	120.2 (3)	C25—C24—C23	117.9 (3)
C11—C10—C13	120.2 (2)	C25—C24—H24	121.0
C9—C10—C13	119.6 (2)	C23—C24—H24	121.0
C12—C11—C10	120.1 (2)	F7—C25—C26	118.6 (3)
C12—C11—H11	120.0	F7—C25—C24	117.5 (3)
C10—C11—H11	120.0	C26—C25—C24	123.9 (3)
C11—C12—C7	120.6 (2)	C25—C26—C27	117.9 (3)
C11—C12—H12	119.7	C25—C26—H26	121.0
C7—C12—H12	119.7	C27—C26—H26	121.0
F2'—C13—F1'	105.2 (8)	C22—C27—C26	119.6 (3)
F2'—C13—F3'	108.7 (7)	C22—C27—H27	120.2
F1'—C13—F3'	103.8 (6)	C26—C27—H27	120.2
F3—C13—F1	105.9 (5)	C5—N1—C1	112.9 (2)
F3—C13—F2	107.9 (5)	C5—N1—S1	120.87 (19)
F1—C13—F2	100.2 (5)	C1—N1—S1	117.40 (18)
F2'—C13—C10	112.7 (5)	O2—S1—O3	119.80 (12)
F3—C13—C10	114.8 (4)	O2—S1—N1	106.01 (12)
F1'—C13—C10	112.3 (4)	O3—S1—N1	106.49 (12)
F3'—C13—C10	113.5 (4)	O2—S1—C22	106.57 (12)
F1—C13—C10	113.5 (4)	O3—S1—C22	109.23 (13)
F2—C13—C10	113.3 (3)	N1—S1—C22	108.28 (11)

N1—C1—C2—C6	−146.5 (3)	C20—C15—C16—C17	−1.3 (4)
N1—C1—C2—C3	30.3 (3)	C14—C15—C16—C17	−176.7 (3)
C6—C2—C3—O1	−9.1 (4)	C15—C16—C17—C18	0.6 (5)
C1—C2—C3—O1	173.9 (2)	C16—C17—C18—C19	0.5 (4)
C6—C2—C3—C4	173.1 (2)	C16—C17—C18—C21	176.9 (3)
C1—C2—C3—C4	−4.0 (4)	C17—C18—C19—C20	−0.9 (4)
O1—C3—C4—C14	5.3 (4)	C21—C18—C19—C20	−177.3 (3)
C2—C3—C4—C14	−176.9 (2)	C18—C19—C20—C15	0.2 (4)
O1—C3—C4—C5	−174.3 (2)	C16—C15—C20—C19	0.9 (4)
C2—C3—C4—C5	3.5 (4)	C14—C15—C20—C19	176.2 (3)
C14—C4—C5—N1	150.8 (3)	C19—C18—C21—F5	−152.5 (3)
C3—C4—C5—N1	−29.6 (3)	C17—C18—C21—F5	31.1 (4)
C3—C2—C6—C7	−176.6 (3)	C19—C18—C21—F4	−28.2 (4)
C1—C2—C6—C7	0.2 (5)	C17—C18—C21—F4	155.4 (3)
C2—C6—C7—C8	151.6 (3)	C19—C18—C21—F6	89.0 (3)
C2—C6—C7—C12	−30.2 (5)	C17—C18—C21—F6	−87.4 (4)
C12—C7—C8—C9	2.6 (4)	C27—C22—C23—C24	0.0 (4)
C6—C7—C8—C9	−179.1 (3)	S1—C22—C23—C24	−178.5 (2)
C7—C8—C9—C10	−0.5 (4)	C22—C23—C24—C25	−0.7 (4)
C8—C9—C10—C11	−1.7 (4)	C23—C24—C25—F7	−178.3 (3)
C8—C9—C10—C13	179.7 (3)	C23—C24—C25—C26	0.5 (5)
C9—C10—C11—C12	1.7 (4)	F7—C25—C26—C27	179.2 (3)
C13—C10—C11—C12	−179.7 (3)	C24—C25—C26—C27	0.4 (5)
C10—C11—C12—C7	0.4 (4)	C23—C22—C27—C26	1.0 (4)
C8—C7—C12—C11	−2.6 (4)	S1—C22—C27—C26	179.5 (2)
C6—C7—C12—C11	179.2 (3)	C25—C26—C27—C22	−1.1 (4)
C11—C10—C13—F2'	73.8 (14)	C4—C5—N1—C1	58.2 (3)
C9—C10—C13—F2'	−107.6 (13)	C4—C5—N1—S1	−88.3 (3)
C11—C10—C13—F3	−89.8 (8)	C2—C1—N1—C5	−58.4 (3)
C9—C10—C13—F3	88.7 (8)	C2—C1—N1—S1	89.4 (2)
C11—C10—C13—F1'	−44.8 (11)	C5—N1—S1—O2	−154.37 (18)
C9—C10—C13—F1'	133.8 (11)	C1—N1—S1—O2	60.6 (2)
C11—C10—C13—F3'	−162.1 (10)	C5—N1—S1—O3	−25.8 (2)
C9—C10—C13—F3'	16.4 (10)	C1—N1—S1—O3	−170.82 (17)
C11—C10—C13—F1	32.2 (6)	C5—N1—S1—C22	91.6 (2)
C9—C10—C13—F1	−149.2 (6)	C1—N1—S1—C22	−53.5 (2)
C11—C10—C13—F2	145.6 (8)	C27—C22—S1—O2	161.2 (2)
C9—C10—C13—F2	−35.8 (9)	C23—C22—S1—O2	−20.3 (3)
C3—C4—C14—C15	−173.1 (3)	C27—C22—S1—O3	30.5 (3)
C5—C4—C14—C15	6.5 (5)	C23—C22—S1—O3	−151.0 (2)
C4—C14—C15—C16	−154.1 (3)	C27—C22—S1—N1	−85.1 (2)
C4—C14—C15—C20	30.7 (4)	C23—C22—S1—N1	93.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C26—H26···O1ⁱ	0.95	2.58	3.458 (3)	154
C23—H23···F2′ⁱⁱ	0.95	2.58	3.364 (12)	140
C23—H23···F1ⁱⁱ	0.95	2.61	3.242 (7)	124
C1—H1B···O1ⁱⁱⁱ	0.99	2.46	3.293 (3)	142

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

(3E,5E)-1-(4-Nitrobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one (6) top

Crystal data top

C₂₇H₁₈F₆N₂O₅S	Z = 2
M_r = 596.49	F(000) = 608
Triclinic, P1	D_x = 1.590 Mg m⁻³
a = 7.4346 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6714 (11) Å	Cell parameters from 5944 reflections
c = 14.6479 (15) Å	θ = 2.3–26.4°
α = 90.825 (5)°	µ = 0.22 mm⁻¹
β = 96.884 (5)°	T = 150 K
γ = 98.971 (5)°	Block, yellow
V = 1245.7 (2) Å³	0.18 × 0.16 × 0.10 mm

Data collection top

Bruker SMART CCD area detector diffractometer	R_int = 0.072
Radiation source: sealed tube	θ_max = 26.0°, θ_min = 2.2°
phi and ω scans	h = −9→9
23092 measured reflections	k = −14→14
4848 independent reflections	l = −18→18
3350 reflections with I > 2σ(I)

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0531P)² + 1.0046P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4848 reflections	Δρ_max = 0.41 e Å⁻³
370 parameters	Δρ_min = −0.41 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2697 (3)	0.2808 (2)	0.99958 (18)	0.0237 (6)
H1A	0.3550	0.3436	1.0356	0.028*
H1B	0.3403	0.2411	0.9594	0.028*
C2	0.1802 (3)	0.1958 (2)	1.06333 (18)	0.0218 (6)
C3	−0.0101 (3)	0.1329 (2)	1.03293 (18)	0.0228 (6)
C4	−0.0992 (4)	0.1547 (2)	0.93983 (18)	0.0233 (6)
C5	0.0042 (4)	0.2409 (2)	0.88225 (18)	0.0244 (6)
H5A	0.0792	0.2012	0.8444	0.029*
H5B	−0.0830	0.2778	0.8404	0.029*
C6	0.2579 (4)	0.1728 (2)	1.14696 (18)	0.0241 (6)
H6	0.1800	0.1231	1.1815	0.029*
C7	0.4435 (3)	0.2119 (2)	1.19402 (18)	0.0226 (6)
C8	0.4688 (4)	0.2154 (3)	1.29007 (19)	0.0310 (7)
H8	0.3655	0.1964	1.3225	0.037*
C9	0.6414 (4)	0.2460 (3)	1.3389 (2)	0.0319 (7)
H9	0.6561	0.2499	1.4043	0.038*
C10	0.7924 (4)	0.2710 (2)	1.29146 (19)	0.0266 (6)
C11	0.7714 (4)	0.2664 (2)	1.19627 (19)	0.0244 (6)
H11	0.8758	0.2830	1.1643	0.029*
C12	0.5980 (4)	0.2377 (2)	1.14770 (19)	0.0242 (6)
H12	0.5839	0.2354	1.0823	0.029*
C13	0.9797 (4)	0.2955 (3)	1.3438 (2)	0.0385 (8)
C14	−0.2679 (4)	0.0956 (2)	0.91185 (19)	0.0248 (6)
H14	−0.3218	0.0480	0.9566	0.030*
C15	−0.3797 (4)	0.0941 (2)	0.82299 (19)	0.0249 (6)
C16	−0.5702 (4)	0.0620 (2)	0.8190 (2)	0.0281 (6)
H16	−0.6225	0.0434	0.8741	0.034*
C17	−0.6826 (4)	0.0571 (2)	0.7373 (2)	0.0347 (7)
H17	−0.8116	0.0367	0.7362	0.042*
C18	−0.6080 (4)	0.0817 (3)	0.6561 (2)	0.0368 (7)
C19	−0.4201 (4)	0.1100 (3)	0.6575 (2)	0.0360 (7)
H19	−0.3687	0.1257	0.6018	0.043*
C20	−0.3071 (4)	0.1154 (2)	0.7399 (2)	0.0298 (6)
H20	−0.1780	0.1339	0.7402	0.036*
C21	−0.7317 (5)	0.0732 (3)	0.5674 (3)	0.0512 (9)
C22	0.2910 (3)	0.4401 (2)	0.80587 (18)	0.0225 (6)
C23	0.4795 (4)	0.4413 (2)	0.82156 (19)	0.0268 (6)
H23	0.5426	0.4528	0.8821	0.032*
C24	0.5737 (4)	0.4254 (2)	0.7475 (2)	0.0317 (7)
H24	0.7028	0.4268	0.7562	0.038*
C25	0.4765 (4)	0.4076 (2)	0.6611 (2)	0.0299 (7)
C26	0.2900 (4)	0.4064 (2)	0.6445 (2)	0.0323 (7)
H26	0.2278	0.3947	0.5838	0.039*
C27	0.1952 (4)	0.4224 (2)	0.71799 (19)	0.0287 (6)
H27	0.0663	0.4214	0.7086	0.034*
F1	1.1028 (2)	0.35879 (16)	1.29868 (14)	0.0502 (5)
F2	1.0477 (2)	0.19669 (19)	1.36152 (16)	0.0626 (7)
F3	0.9829 (3)	0.3491 (3)	1.42395 (16)	0.0943 (10)
F4	−0.6494 (4)	0.1212 (3)	0.49823 (18)	0.1085 (12)
F5	−0.8768 (4)	0.1228 (3)	0.5723 (2)	0.1092 (11)
F6	−0.7900 (3)	−0.03590 (19)	0.53857 (15)	0.0697 (7)
N1	0.1234 (3)	0.32961 (18)	0.94353 (15)	0.0233 (5)
N2	0.5775 (4)	0.3884 (2)	0.5824 (2)	0.0431 (7)
O1	−0.0883 (2)	0.06280 (16)	1.08281 (13)	0.0290 (5)
O2	0.2915 (2)	0.52922 (15)	0.96959 (12)	0.0265 (4)
O3	−0.0020 (2)	0.48987 (16)	0.86577 (13)	0.0277 (4)
O4	0.7417 (3)	0.3840 (2)	0.59848 (18)	0.0606 (7)
O5	0.4897 (4)	0.3747 (2)	0.50595 (18)	0.0665 (8)
S1	0.16976 (9)	0.45813 (6)	0.90097 (5)	0.02288 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0206 (13)	0.0262 (14)	0.0226 (14)	0.0013 (11)	−0.0016 (11)	0.0016 (11)
C2	0.0223 (13)	0.0209 (13)	0.0217 (14)	0.0014 (10)	0.0033 (11)	0.0011 (11)
C3	0.0226 (14)	0.0251 (14)	0.0213 (14)	0.0033 (11)	0.0058 (11)	−0.0011 (11)
C4	0.0231 (14)	0.0232 (14)	0.0223 (14)	0.0019 (11)	0.0000 (11)	−0.0008 (11)
C5	0.0227 (14)	0.0261 (14)	0.0209 (14)	−0.0019 (11)	−0.0037 (11)	−0.0004 (11)
C6	0.0226 (14)	0.0263 (14)	0.0241 (15)	0.0032 (11)	0.0060 (12)	0.0022 (11)
C7	0.0207 (13)	0.0231 (13)	0.0241 (14)	0.0049 (11)	0.0005 (11)	0.0050 (11)
C8	0.0251 (15)	0.0452 (17)	0.0244 (16)	0.0095 (13)	0.0035 (12)	0.0077 (13)
C9	0.0290 (15)	0.0486 (18)	0.0200 (15)	0.0157 (13)	−0.0015 (12)	0.0022 (13)
C10	0.0250 (14)	0.0279 (15)	0.0275 (15)	0.0096 (11)	−0.0016 (12)	0.0009 (12)
C11	0.0215 (14)	0.0253 (14)	0.0273 (15)	0.0054 (11)	0.0041 (12)	0.0012 (11)
C12	0.0270 (14)	0.0235 (14)	0.0226 (14)	0.0046 (11)	0.0043 (12)	0.0010 (11)
C13	0.0276 (16)	0.056 (2)	0.0327 (18)	0.0130 (15)	−0.0020 (14)	0.0042 (15)
C14	0.0260 (14)	0.0225 (14)	0.0255 (15)	0.0025 (11)	0.0035 (12)	−0.0008 (11)
C15	0.0212 (14)	0.0195 (13)	0.0309 (16)	−0.0018 (11)	−0.0027 (12)	−0.0011 (11)
C16	0.0238 (14)	0.0237 (14)	0.0354 (17)	0.0001 (11)	0.0025 (13)	0.0005 (12)
C17	0.0231 (15)	0.0285 (16)	0.048 (2)	0.0009 (12)	−0.0087 (14)	−0.0014 (14)
C18	0.0375 (17)	0.0289 (16)	0.0375 (18)	0.0003 (13)	−0.0162 (14)	0.0029 (13)
C19	0.0390 (17)	0.0338 (16)	0.0294 (17)	−0.0060 (13)	−0.0039 (14)	0.0019 (13)
C20	0.0234 (14)	0.0318 (15)	0.0306 (16)	−0.0035 (12)	−0.0007 (12)	−0.0010 (12)
C21	0.049 (2)	0.044 (2)	0.050 (2)	−0.0060 (17)	−0.0198 (18)	0.0045 (17)
C22	0.0234 (14)	0.0209 (13)	0.0223 (14)	0.0018 (11)	0.0016 (11)	0.0019 (11)
C23	0.0269 (15)	0.0294 (15)	0.0226 (15)	0.0007 (11)	0.0017 (12)	0.0012 (11)
C24	0.0271 (15)	0.0328 (16)	0.0363 (18)	0.0060 (12)	0.0069 (13)	0.0028 (13)
C25	0.0362 (16)	0.0265 (15)	0.0289 (16)	0.0049 (12)	0.0124 (13)	−0.0017 (12)
C26	0.0381 (17)	0.0363 (16)	0.0214 (15)	0.0044 (13)	0.0014 (13)	0.0008 (12)
C27	0.0246 (14)	0.0341 (16)	0.0270 (16)	0.0053 (12)	0.0001 (12)	0.0028 (12)
F1	0.0271 (10)	0.0541 (12)	0.0628 (13)	−0.0043 (8)	−0.0087 (9)	0.0168 (10)
F2	0.0273 (10)	0.0755 (15)	0.0861 (17)	0.0151 (10)	−0.0017 (10)	0.0436 (13)
F3	0.0377 (12)	0.185 (3)	0.0528 (15)	0.0176 (15)	−0.0155 (11)	−0.0596 (17)
F4	0.095 (2)	0.135 (2)	0.0626 (17)	−0.0474 (18)	−0.0445 (15)	0.0581 (17)
F5	0.090 (2)	0.134 (3)	0.099 (2)	0.0623 (19)	−0.0620 (17)	−0.0291 (18)
F6	0.0825 (16)	0.0577 (14)	0.0514 (14)	−0.0123 (12)	−0.0309 (12)	−0.0028 (10)
N1	0.0222 (12)	0.0226 (12)	0.0227 (12)	−0.0013 (9)	−0.0014 (10)	0.0052 (9)
N2	0.0588 (19)	0.0370 (15)	0.0371 (17)	0.0057 (13)	0.0235 (15)	−0.0053 (12)
O1	0.0271 (10)	0.0322 (11)	0.0261 (11)	−0.0026 (8)	0.0056 (9)	0.0045 (8)
O2	0.0298 (10)	0.0256 (10)	0.0217 (10)	−0.0017 (8)	0.0016 (8)	−0.0017 (8)
O3	0.0228 (10)	0.0318 (11)	0.0290 (11)	0.0072 (8)	0.0012 (8)	0.0060 (8)
O4	0.0484 (16)	0.0762 (19)	0.0636 (18)	0.0120 (13)	0.0315 (14)	−0.0027 (14)
O5	0.083 (2)	0.088 (2)	0.0329 (15)	0.0161 (16)	0.0222 (15)	−0.0119 (14)
S1	0.0228 (3)	0.0246 (3)	0.0204 (4)	0.0017 (3)	0.0020 (3)	0.0024 (3)

Geometric parameters (Å, º) top

C1—N1	1.474 (3)	C15—C20	1.400 (4)
C1—C2	1.507 (3)	C15—C16	1.402 (4)
C1—H1A	0.9900	C16—C17	1.370 (4)
C1—H1B	0.9900	C16—H16	0.9500
C2—C6	1.339 (4)	C17—C18	1.386 (4)
C2—C3	1.501 (4)	C17—H17	0.9500
C3—O1	1.230 (3)	C18—C19	1.383 (4)
C3—C4	1.486 (4)	C18—C21	1.491 (4)
C4—C14	1.348 (4)	C19—C20	1.379 (4)
C4—C5	1.502 (4)	C19—H19	0.9500
C5—N1	1.469 (3)	C20—H20	0.9500
C5—H5A	0.9900	C21—F5	1.310 (4)
C5—H5B	0.9900	C21—F6	1.325 (4)
C6—C7	1.468 (4)	C21—F4	1.331 (4)
C6—H6	0.9500	C22—C23	1.390 (4)
C7—C8	1.396 (4)	C22—C27	1.391 (4)
C7—C12	1.398 (4)	C22—S1	1.775 (3)
C8—C9	1.384 (4)	C23—C24	1.385 (4)
C8—H8	0.9500	C23—H23	0.9500
C9—C10	1.385 (4)	C24—C25	1.376 (4)
C9—H9	0.9500	C24—H24	0.9500
C10—C11	1.384 (4)	C25—C26	1.376 (4)
C10—C13	1.491 (4)	C25—N2	1.481 (4)
C11—C12	1.385 (4)	C26—C27	1.381 (4)
C11—H11	0.9500	C26—H26	0.9500
C12—H12	0.9500	C27—H27	0.9500
C13—F3	1.318 (4)	N1—S1	1.635 (2)
C13—F1	1.329 (4)	N2—O5	1.222 (4)
C13—F2	1.347 (4)	N2—O4	1.224 (4)
C14—C15	1.456 (4)	O2—S1	1.4290 (19)
C14—H14	0.9500	O3—S1	1.4246 (19)

N1—C1—C2	107.8 (2)	C16—C15—C14	118.5 (3)
N1—C1—H1A	110.1	C17—C16—C15	121.3 (3)
C2—C1—H1A	110.1	C17—C16—H16	119.4
N1—C1—H1B	110.1	C15—C16—H16	119.4
C2—C1—H1B	110.1	C16—C17—C18	120.0 (3)
H1A—C1—H1B	108.5	C16—C17—H17	120.0
C6—C2—C3	116.9 (2)	C18—C17—H17	120.0
C6—C2—C1	124.4 (2)	C19—C18—C17	120.0 (3)
C3—C2—C1	118.7 (2)	C19—C18—C21	120.6 (3)
O1—C3—C4	120.8 (2)	C17—C18—C21	119.4 (3)
O1—C3—C2	120.8 (2)	C20—C19—C18	120.0 (3)
C4—C3—C2	118.3 (2)	C20—C19—H19	120.0
C14—C4—C3	118.1 (2)	C18—C19—H19	120.0
C14—C4—C5	123.8 (2)	C19—C20—C15	121.1 (3)
C3—C4—C5	118.1 (2)	C19—C20—H20	119.5
N1—C5—C4	108.8 (2)	C15—C20—H20	119.5
N1—C5—H5A	109.9	F5—C21—F6	107.5 (3)
C4—C5—H5A	109.9	F5—C21—F4	106.6 (3)
N1—C5—H5B	109.9	F6—C21—F4	104.0 (3)
C4—C5—H5B	109.9	F5—C21—C18	112.8 (3)
H5A—C5—H5B	108.3	F6—C21—C18	112.1 (3)
C2—C6—C7	130.6 (2)	F4—C21—C18	113.2 (3)
C2—C6—H6	114.7	C23—C22—C27	121.6 (3)
C7—C6—H6	114.7	C23—C22—S1	119.0 (2)
C8—C7—C12	118.4 (2)	C27—C22—S1	119.4 (2)
C8—C7—C6	118.2 (2)	C24—C23—C22	119.0 (3)
C12—C7—C6	123.3 (2)	C24—C23—H23	120.5
C9—C8—C7	121.3 (3)	C22—C23—H23	120.5
C9—C8—H8	119.4	C25—C24—C23	118.6 (3)
C7—C8—H8	119.4	C25—C24—H24	120.7
C8—C9—C10	119.3 (3)	C23—C24—H24	120.7
C8—C9—H9	120.4	C26—C25—C24	123.0 (3)
C10—C9—H9	120.4	C26—C25—N2	118.6 (3)
C11—C10—C9	120.6 (3)	C24—C25—N2	118.4 (3)
C11—C10—C13	119.9 (2)	C25—C26—C27	118.7 (3)
C9—C10—C13	119.4 (3)	C25—C26—H26	120.7
C10—C11—C12	119.9 (2)	C27—C26—H26	120.7
C10—C11—H11	120.0	C26—C27—C22	119.1 (3)
C12—C11—H11	120.0	C26—C27—H27	120.5
C11—C12—C7	120.6 (2)	C22—C27—H27	120.5
C11—C12—H12	119.7	C5—N1—C1	111.8 (2)
C7—C12—H12	119.7	C5—N1—S1	116.02 (17)
F3—C13—F1	107.2 (3)	C1—N1—S1	119.59 (17)
F3—C13—F2	106.5 (3)	O5—N2—O4	124.4 (3)
F1—C13—F2	104.8 (2)	O5—N2—C25	117.5 (3)
F3—C13—C10	112.9 (3)	O4—N2—C25	118.1 (3)
F1—C13—C10	113.8 (2)	O3—S1—O2	120.83 (12)
F2—C13—C10	111.1 (3)	O3—S1—N1	106.37 (11)
C4—C14—C15	129.4 (3)	O2—S1—N1	107.05 (11)
C4—C14—H14	115.3	O3—S1—C22	107.42 (12)
C15—C14—H14	115.3	O2—S1—C22	107.99 (12)
C20—C15—C16	117.6 (3)	N1—S1—C22	106.35 (12)
C20—C15—C14	123.8 (2)

N1—C1—C2—C6	−149.6 (3)	C17—C18—C19—C20	−1.0 (4)
N1—C1—C2—C3	29.4 (3)	C21—C18—C19—C20	−178.8 (3)
C6—C2—C3—O1	−0.8 (4)	C18—C19—C20—C15	−0.8 (4)
C1—C2—C3—O1	−180.0 (2)	C16—C15—C20—C19	2.8 (4)
C6—C2—C3—C4	−178.9 (2)	C14—C15—C20—C19	178.4 (3)
C1—C2—C3—C4	2.0 (4)	C19—C18—C21—F5	−136.3 (3)
O1—C3—C4—C14	0.1 (4)	C17—C18—C21—F5	45.9 (4)
C2—C3—C4—C14	178.2 (2)	C19—C18—C21—F6	102.2 (4)
O1—C3—C4—C5	−179.7 (2)	C17—C18—C21—F6	−75.6 (4)
C2—C3—C4—C5	−1.6 (4)	C19—C18—C21—F4	−15.1 (5)
C14—C4—C5—N1	149.9 (3)	C17—C18—C21—F4	167.1 (3)
C3—C4—C5—N1	−30.3 (3)	C27—C22—C23—C24	0.5 (4)
C3—C2—C6—C7	174.9 (2)	S1—C22—C23—C24	179.0 (2)
C1—C2—C6—C7	−6.0 (5)	C22—C23—C24—C25	−0.8 (4)
C2—C6—C7—C8	154.6 (3)	C23—C24—C25—C26	0.9 (4)
C2—C6—C7—C12	−30.2 (4)	C23—C24—C25—N2	−178.9 (2)
C12—C7—C8—C9	1.4 (4)	C24—C25—C26—C27	−0.8 (4)
C6—C7—C8—C9	176.9 (3)	N2—C25—C26—C27	179.0 (2)
C7—C8—C9—C10	−1.5 (4)	C25—C26—C27—C22	0.5 (4)
C8—C9—C10—C11	0.5 (4)	C23—C22—C27—C26	−0.4 (4)
C8—C9—C10—C13	−175.5 (3)	S1—C22—C27—C26	−178.8 (2)
C9—C10—C11—C12	0.6 (4)	C4—C5—N1—C1	66.3 (3)
C13—C10—C11—C12	176.6 (2)	C4—C5—N1—S1	−151.72 (18)
C10—C11—C12—C7	−0.7 (4)	C2—C1—N1—C5	−65.4 (3)
C8—C7—C12—C11	−0.3 (4)	C2—C1—N1—S1	154.18 (18)
C6—C7—C12—C11	−175.5 (2)	C26—C25—N2—O5	1.4 (4)
C11—C10—C13—F3	150.4 (3)	C24—C25—N2—O5	−178.8 (3)
C9—C10—C13—F3	−33.6 (4)	C26—C25—N2—O4	−176.5 (3)
C11—C10—C13—F1	27.9 (4)	C24—C25—N2—O4	3.3 (4)
C9—C10—C13—F1	−156.0 (3)	C5—N1—S1—O3	51.6 (2)
C11—C10—C13—F2	−90.1 (3)	C1—N1—S1—O3	−169.49 (19)
C9—C10—C13—F2	86.0 (3)	C5—N1—S1—O2	−177.90 (18)
C3—C4—C14—C15	−175.3 (3)	C1—N1—S1—O2	−39.0 (2)
C5—C4—C14—C15	4.5 (5)	C5—N1—S1—C22	−62.6 (2)
C4—C14—C15—C20	27.5 (5)	C1—N1—S1—C22	76.2 (2)
C4—C14—C15—C16	−157.0 (3)	C23—C22—S1—O3	162.1 (2)
C20—C15—C16—C17	−3.1 (4)	C27—C22—S1—O3	−19.4 (2)
C14—C15—C16—C17	−178.9 (3)	C23—C22—S1—O2	30.3 (2)
C15—C16—C17—C18	1.3 (4)	C27—C22—S1—O2	−151.2 (2)
C16—C17—C18—C19	0.7 (4)	C23—C22—S1—N1	−84.4 (2)
C16—C17—C18—C21	178.6 (3)	C27—C22—S1—N1	94.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24···O3ⁱ	0.95	2.56	3.380 (4)	145
C23—H23···O2ⁱⁱ	0.95	2.36	3.304 (3)	176

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

(3E,5E)-1-(4-Cyanobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one dichloromethane monosolvate (7) top

Crystal data top

C₂₈H₁₈F₆N₂O₃S·CH₂Cl₂	Z = 2
M_r = 661.43	F(000) = 672
Triclinic, P1	D_x = 1.536 Mg m⁻³
a = 9.7338 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.4558 (9) Å	Cell parameters from 5958 reflections
c = 12.6397 (9) Å	θ = 2.6–26.5°
α = 70.586 (3)°	µ = 0.38 mm⁻¹
β = 88.379 (4)°	T = 150 K
γ = 81.726 (3)°	Block, yellow
V = 1429.97 (17) Å³	0.20 × 0.15 × 0.11 mm

Data collection top

Bruker SMART CCD area detector diffractometer	R_int = 0.070
Radiation source: sealed tube	θ_max = 26.0°, θ_min = 2.6°
phi and ω scans	h = −12→12
24790 measured reflections	k = −15→15
5604 independent reflections	l = −15→15
3869 reflections with I > 2σ(I)

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0465P)² + 0.7221P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
5604 reflections	Δρ_max = 0.53 e Å⁻³
388 parameters	Δρ_min = −0.44 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2251 (3)	0.6874 (2)	0.3737 (2)	0.0239 (6)
H1A	0.3181	0.7010	0.3429	0.029*
H1B	0.1587	0.7048	0.3104	0.029*
C2	0.2295 (2)	0.5639 (2)	0.4483 (2)	0.0203 (5)
C3	0.1347 (3)	0.5379 (2)	0.5467 (2)	0.0228 (6)
C4	0.0349 (2)	0.6341 (2)	0.5613 (2)	0.0203 (5)
C5	0.0378 (2)	0.7528 (2)	0.4781 (2)	0.0221 (5)
H5A	−0.0243	0.7657	0.4131	0.027*
H5B	0.0057	0.8116	0.5136	0.027*
C6	0.3168 (2)	0.4754 (2)	0.4360 (2)	0.0222 (6)
H6	0.3107	0.4028	0.4912	0.027*
C7	0.4201 (2)	0.4745 (2)	0.3497 (2)	0.0214 (5)
C8	0.5350 (3)	0.3884 (2)	0.3780 (2)	0.0239 (6)
H8	0.5408	0.3317	0.4505	0.029*
C9	0.6399 (3)	0.3837 (2)	0.3037 (2)	0.0249 (6)
H9	0.7181	0.3254	0.3255	0.030*
C10	0.6306 (3)	0.4647 (2)	0.1966 (2)	0.0230 (6)
C11	0.5137 (3)	0.5474 (2)	0.1649 (2)	0.0253 (6)
H11	0.5054	0.6010	0.0908	0.030*
C12	0.4095 (3)	0.5524 (2)	0.2400 (2)	0.0238 (6)
H12	0.3300	0.6092	0.2172	0.029*
C13	0.7436 (3)	0.4651 (2)	0.1152 (2)	0.0306 (6)
C14	−0.0505 (3)	0.6104 (2)	0.6484 (2)	0.0238 (6)
H14	−0.0352	0.5338	0.6993	0.029*
C15	−0.1642 (2)	0.6869 (2)	0.6756 (2)	0.0232 (6)
C16	−0.2007 (3)	0.6650 (2)	0.7880 (2)	0.0318 (6)
H16	−0.1463	0.6056	0.8451	0.038*
C17	−0.3144 (3)	0.7282 (3)	0.8170 (2)	0.0348 (7)
H17	−0.3365	0.7136	0.8937	0.042*
C18	−0.3965 (3)	0.8132 (2)	0.7342 (2)	0.0278 (6)
C19	−0.3622 (3)	0.8373 (2)	0.6225 (2)	0.0275 (6)
H19	−0.4180	0.8960	0.5658	0.033*
C20	−0.2459 (2)	0.7755 (2)	0.5939 (2)	0.0246 (6)
H20	−0.2213	0.7936	0.5174	0.030*
C21	−0.5244 (3)	0.8746 (3)	0.7680 (3)	0.0353 (7)
C22	0.1465 (2)	0.9772 (2)	0.2868 (2)	0.0199 (5)
C23	0.1993 (3)	0.9807 (2)	0.1829 (2)	0.0257 (6)
H23	0.2846	0.9350	0.1780	0.031*
C24	0.1271 (3)	1.0512 (2)	0.0868 (2)	0.0319 (6)
H24	0.1629	1.0550	0.0152	0.038*
C25	0.0013 (3)	1.1169 (2)	0.0953 (2)	0.0294 (6)
C26	−0.0518 (3)	1.1122 (2)	0.1996 (2)	0.0303 (6)
H26	−0.1380	1.1568	0.2048	0.036*
C27	0.0212 (3)	1.0423 (2)	0.2959 (2)	0.0264 (6)
H27	−0.0140	1.0388	0.3676	0.032*
C28	−0.0742 (3)	1.1910 (3)	−0.0048 (3)	0.0447 (8)
C29	0.3476 (3)	0.2120 (3)	0.7732 (2)	0.0421 (8)
H29A	0.4133	0.1976	0.7166	0.050*
H29B	0.3169	0.2960	0.7507	0.050*
Cl1	0.20281 (8)	0.14143 (7)	0.77593 (7)	0.0483 (2)
Cl2	0.43281 (8)	0.16459 (7)	0.90498 (7)	0.0445 (2)
F1	0.80484 (18)	0.56012 (16)	0.08932 (16)	0.0527 (5)
F2	0.69830 (18)	0.46293 (18)	0.01714 (14)	0.0535 (5)
F3	0.84560 (17)	0.37668 (15)	0.15218 (14)	0.0473 (5)
F4	−0.60578 (18)	0.9403 (2)	0.68140 (16)	0.0634 (6)
F5	−0.49708 (16)	0.94232 (15)	0.82446 (15)	0.0434 (4)
F6	−0.60193 (18)	0.80030 (17)	0.83699 (19)	0.0636 (6)
N1	0.1814 (2)	0.76125 (17)	0.44130 (16)	0.0208 (5)
N2	−0.1347 (3)	1.2483 (3)	−0.0848 (2)	0.0687 (10)
O1	0.1362 (2)	0.43929 (15)	0.61050 (15)	0.0326 (5)
O2	0.38056 (16)	0.86676 (15)	0.38543 (14)	0.0261 (4)
O3	0.19401 (18)	0.92877 (15)	0.49955 (14)	0.0278 (4)
S1	0.23658 (6)	0.88541 (5)	0.41058 (5)	0.02072 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0293 (14)	0.0212 (14)	0.0206 (13)	−0.0014 (11)	0.0024 (11)	−0.0073 (11)
C2	0.0221 (12)	0.0201 (13)	0.0180 (12)	−0.0031 (10)	−0.0042 (10)	−0.0048 (10)
C3	0.0272 (14)	0.0213 (14)	0.0206 (13)	−0.0073 (11)	−0.0010 (11)	−0.0059 (11)
C4	0.0225 (13)	0.0215 (13)	0.0174 (12)	−0.0061 (10)	−0.0003 (10)	−0.0058 (11)
C5	0.0219 (13)	0.0204 (13)	0.0210 (13)	−0.0039 (10)	0.0017 (10)	−0.0027 (11)
C6	0.0262 (13)	0.0190 (13)	0.0201 (13)	−0.0050 (11)	−0.0051 (10)	−0.0035 (11)
C7	0.0247 (13)	0.0189 (13)	0.0220 (13)	−0.0053 (11)	−0.0042 (10)	−0.0073 (11)
C8	0.0275 (14)	0.0222 (14)	0.0199 (13)	−0.0037 (11)	−0.0038 (11)	−0.0036 (11)
C9	0.0245 (13)	0.0231 (14)	0.0251 (14)	0.0003 (11)	−0.0047 (11)	−0.0066 (11)
C10	0.0255 (13)	0.0227 (14)	0.0229 (13)	−0.0055 (11)	−0.0027 (11)	−0.0091 (11)
C11	0.0314 (14)	0.0225 (14)	0.0192 (13)	−0.0015 (11)	−0.0018 (11)	−0.0039 (11)
C12	0.0251 (13)	0.0209 (14)	0.0225 (13)	0.0025 (11)	−0.0050 (11)	−0.0054 (11)
C13	0.0306 (15)	0.0306 (16)	0.0286 (15)	−0.0009 (12)	−0.0007 (12)	−0.0086 (13)
C14	0.0285 (13)	0.0197 (14)	0.0222 (13)	−0.0059 (11)	−0.0011 (11)	−0.0042 (11)
C15	0.0234 (13)	0.0230 (14)	0.0254 (14)	−0.0096 (11)	0.0033 (11)	−0.0086 (11)
C16	0.0301 (15)	0.0357 (17)	0.0250 (15)	−0.0018 (12)	0.0021 (12)	−0.0054 (13)
C17	0.0306 (15)	0.0457 (19)	0.0275 (15)	−0.0038 (14)	0.0050 (12)	−0.0125 (14)
C18	0.0224 (13)	0.0310 (16)	0.0363 (16)	−0.0080 (12)	0.0024 (12)	−0.0179 (13)
C19	0.0251 (14)	0.0252 (15)	0.0328 (15)	−0.0066 (11)	−0.0018 (12)	−0.0089 (12)
C20	0.0255 (14)	0.0252 (14)	0.0237 (14)	−0.0105 (11)	0.0030 (11)	−0.0062 (11)
C21	0.0297 (15)	0.0407 (18)	0.0408 (17)	−0.0069 (13)	0.0039 (13)	−0.0198 (15)
C22	0.0196 (12)	0.0157 (13)	0.0228 (13)	−0.0040 (10)	−0.0013 (10)	−0.0034 (10)
C23	0.0245 (13)	0.0257 (15)	0.0233 (14)	0.0000 (11)	0.0008 (11)	−0.0049 (12)
C24	0.0366 (16)	0.0353 (17)	0.0202 (14)	−0.0016 (13)	−0.0018 (12)	−0.0058 (12)
C25	0.0319 (15)	0.0248 (15)	0.0285 (15)	0.0014 (12)	−0.0098 (12)	−0.0065 (12)
C26	0.0242 (14)	0.0263 (15)	0.0385 (17)	0.0034 (11)	−0.0038 (12)	−0.0109 (13)
C27	0.0283 (14)	0.0240 (14)	0.0257 (14)	−0.0026 (11)	0.0040 (11)	−0.0071 (12)
C28	0.051 (2)	0.0412 (19)	0.0376 (18)	0.0107 (15)	−0.0149 (15)	−0.0138 (16)
C29	0.0449 (18)	0.0406 (19)	0.0347 (17)	−0.0071 (15)	−0.0006 (14)	−0.0040 (15)
Cl1	0.0446 (4)	0.0553 (5)	0.0397 (4)	−0.0100 (4)	−0.0125 (3)	−0.0065 (4)
Cl2	0.0505 (5)	0.0391 (5)	0.0454 (5)	−0.0031 (4)	−0.0147 (4)	−0.0159 (4)
F1	0.0508 (11)	0.0464 (12)	0.0633 (13)	−0.0214 (9)	0.0239 (9)	−0.0172 (10)
F2	0.0449 (10)	0.0923 (16)	0.0309 (9)	−0.0074 (10)	0.0034 (8)	−0.0314 (10)
F3	0.0391 (10)	0.0484 (11)	0.0426 (10)	0.0122 (8)	0.0094 (8)	−0.0077 (9)
F4	0.0376 (10)	0.0985 (17)	0.0558 (12)	0.0263 (10)	−0.0150 (9)	−0.0415 (12)
F5	0.0393 (10)	0.0466 (11)	0.0543 (11)	−0.0010 (8)	0.0011 (8)	−0.0318 (9)
F6	0.0409 (10)	0.0520 (13)	0.1059 (17)	−0.0171 (9)	0.0368 (11)	−0.0352 (12)
N1	0.0243 (11)	0.0163 (11)	0.0204 (11)	−0.0036 (9)	0.0016 (9)	−0.0042 (9)
N2	0.085 (2)	0.066 (2)	0.0404 (17)	0.0332 (18)	−0.0275 (17)	−0.0141 (16)
O1	0.0449 (12)	0.0198 (10)	0.0270 (10)	−0.0033 (8)	0.0094 (9)	−0.0011 (8)
O2	0.0189 (9)	0.0283 (10)	0.0272 (10)	−0.0040 (8)	−0.0005 (7)	−0.0036 (8)
O3	0.0376 (10)	0.0269 (10)	0.0216 (9)	−0.0077 (8)	0.0009 (8)	−0.0102 (8)
S1	0.0228 (3)	0.0200 (3)	0.0176 (3)	−0.0044 (2)	−0.0008 (2)	−0.0033 (3)

Geometric parameters (Å, º) top

C1—N1	1.465 (3)	C16—C17	1.378 (4)
C1—C2	1.508 (3)	C16—H16	0.9500
C1—H1A	0.9900	C17—C18	1.386 (4)
C1—H1B	0.9900	C17—H17	0.9500
C2—C6	1.341 (3)	C18—C19	1.384 (4)
C2—C3	1.502 (3)	C18—C21	1.494 (4)
C3—O1	1.223 (3)	C19—C20	1.384 (4)
C3—C4	1.488 (3)	C19—H19	0.9500
C4—C14	1.340 (3)	C20—H20	0.9500
C4—C5	1.506 (3)	C21—F4	1.328 (3)
C5—N1	1.468 (3)	C21—F5	1.329 (3)
C5—H5A	0.9900	C21—F6	1.347 (3)
C5—H5B	0.9900	C22—C23	1.385 (3)
C6—C7	1.464 (3)	C22—C27	1.388 (3)
C6—H6	0.9500	C22—S1	1.768 (2)
C7—C8	1.396 (3)	C23—C24	1.379 (3)
C7—C12	1.400 (3)	C23—H23	0.9500
C8—C9	1.376 (3)	C24—C25	1.394 (4)
C8—H8	0.9500	C24—H24	0.9500
C9—C10	1.390 (3)	C25—C26	1.387 (4)
C9—H9	0.9500	C25—C28	1.440 (4)
C10—C11	1.390 (3)	C26—C27	1.383 (4)
C10—C13	1.484 (4)	C26—H26	0.9500
C11—C12	1.378 (3)	C27—H27	0.9500
C11—H11	0.9500	C28—N2	1.145 (4)
C12—H12	0.9500	C29—Cl2	1.759 (3)
C13—F2	1.337 (3)	C29—Cl1	1.759 (3)
C13—F3	1.337 (3)	C29—H29A	0.9900
C13—F1	1.341 (3)	C29—H29B	0.9900
C14—C15	1.464 (4)	N1—S1	1.631 (2)
C14—H14	0.9500	O2—S1	1.4315 (17)
C15—C20	1.398 (3)	O3—S1	1.4286 (18)
C15—C16	1.400 (4)

N1—C1—C2	108.13 (19)	C17—C16—H16	119.5
N1—C1—H1A	110.1	C15—C16—H16	119.5
C2—C1—H1A	110.1	C16—C17—C18	120.0 (3)
N1—C1—H1B	110.1	C16—C17—H17	120.0
C2—C1—H1B	110.1	C18—C17—H17	120.0
H1A—C1—H1B	108.4	C19—C18—C17	120.2 (2)
C6—C2—C3	117.1 (2)	C19—C18—C21	121.2 (3)
C6—C2—C1	124.5 (2)	C17—C18—C21	118.6 (2)
C3—C2—C1	118.3 (2)	C20—C19—C18	119.6 (2)
O1—C3—C4	121.1 (2)	C20—C19—H19	120.2
O1—C3—C2	120.6 (2)	C18—C19—H19	120.2
C4—C3—C2	118.3 (2)	C19—C20—C15	121.2 (2)
C14—C4—C3	118.1 (2)	C19—C20—H20	119.4
C14—C4—C5	123.9 (2)	C15—C20—H20	119.4
C3—C4—C5	117.9 (2)	F4—C21—F5	106.6 (2)
N1—C5—C4	107.7 (2)	F4—C21—F6	106.9 (2)
N1—C5—H5A	110.2	F5—C21—F6	105.2 (2)
C4—C5—H5A	110.2	F4—C21—C18	113.1 (2)
N1—C5—H5B	110.2	F5—C21—C18	113.0 (2)
C4—C5—H5B	110.2	F6—C21—C18	111.5 (2)
H5A—C5—H5B	108.5	C23—C22—C27	121.2 (2)
C2—C6—C7	129.4 (2)	C23—C22—S1	119.91 (19)
C2—C6—H6	115.3	C27—C22—S1	118.91 (19)
C7—C6—H6	115.3	C24—C23—C22	119.5 (2)
C8—C7—C12	117.9 (2)	C24—C23—H23	120.3
C8—C7—C6	117.8 (2)	C22—C23—H23	120.3
C12—C7—C6	124.3 (2)	C23—C24—C25	119.7 (3)
C9—C8—C7	121.7 (2)	C23—C24—H24	120.2
C9—C8—H8	119.2	C25—C24—H24	120.2
C7—C8—H8	119.2	C26—C25—C24	120.6 (2)
C8—C9—C10	119.6 (2)	C26—C25—C28	119.5 (3)
C8—C9—H9	120.2	C24—C25—C28	119.9 (3)
C10—C9—H9	120.2	C27—C26—C25	119.7 (2)
C11—C10—C9	119.5 (2)	C27—C26—H26	120.2
C11—C10—C13	119.2 (2)	C25—C26—H26	120.2
C9—C10—C13	121.3 (2)	C26—C27—C22	119.4 (2)
C12—C11—C10	120.6 (2)	C26—C27—H27	120.3
C12—C11—H11	119.7	C22—C27—H27	120.3
C10—C11—H11	119.7	N2—C28—C25	178.9 (4)
C11—C12—C7	120.5 (2)	Cl2—C29—Cl1	111.56 (16)
C11—C12—H12	119.8	Cl2—C29—H29A	109.3
C7—C12—H12	119.8	Cl1—C29—H29A	109.3
F2—C13—F3	106.7 (2)	Cl2—C29—H29B	109.3
F2—C13—F1	105.2 (2)	Cl1—C29—H29B	109.3
F3—C13—F1	105.8 (2)	H29A—C29—H29B	108.0
F2—C13—C10	112.8 (2)	C1—N1—C5	111.55 (19)
F3—C13—C10	113.6 (2)	C1—N1—S1	119.52 (16)
F1—C13—C10	112.2 (2)	C5—N1—S1	118.39 (16)
C4—C14—C15	128.6 (2)	O3—S1—O2	120.45 (11)
C4—C14—H14	115.7	O3—S1—N1	106.35 (10)
C15—C14—H14	115.7	O2—S1—N1	106.35 (11)
C20—C15—C16	117.9 (2)	O3—S1—C22	107.96 (11)
C20—C15—C14	123.1 (2)	O2—S1—C22	108.23 (11)
C16—C15—C14	118.8 (2)	N1—S1—C22	106.76 (11)
C17—C16—C15	121.0 (3)

N1—C1—C2—C6	−149.1 (2)	C16—C17—C18—C19	−2.1 (4)
N1—C1—C2—C3	27.8 (3)	C16—C17—C18—C21	175.9 (3)
C6—C2—C3—O1	−1.6 (4)	C17—C18—C19—C20	0.5 (4)
C1—C2—C3—O1	−178.8 (2)	C21—C18—C19—C20	−177.4 (2)
C6—C2—C3—C4	−178.9 (2)	C18—C19—C20—C15	1.6 (4)
C1—C2—C3—C4	3.9 (3)	C16—C15—C20—C19	−2.1 (4)
O1—C3—C4—C14	2.0 (4)	C14—C15—C20—C19	172.5 (2)
C2—C3—C4—C14	179.3 (2)	C19—C18—C21—F4	8.1 (4)
O1—C3—C4—C5	−179.0 (2)	C17—C18—C21—F4	−169.8 (3)
C2—C3—C4—C5	−1.7 (3)	C19—C18—C21—F5	−113.1 (3)
C14—C4—C5—N1	147.1 (2)	C17—C18—C21—F5	68.9 (3)
C3—C4—C5—N1	−31.9 (3)	C19—C18—C21—F6	128.6 (3)
C3—C2—C6—C7	−179.8 (2)	C17—C18—C21—F6	−49.4 (3)
C1—C2—C6—C7	−2.8 (4)	C27—C22—C23—C24	0.8 (4)
C2—C6—C7—C8	153.1 (3)	S1—C22—C23—C24	179.0 (2)
C2—C6—C7—C12	−28.6 (4)	C22—C23—C24—C25	−0.7 (4)
C12—C7—C8—C9	4.2 (4)	C23—C24—C25—C26	0.1 (4)
C6—C7—C8—C9	−177.4 (2)	C23—C24—C25—C28	179.8 (3)
C7—C8—C9—C10	−1.5 (4)	C24—C25—C26—C27	0.5 (4)
C8—C9—C10—C11	−1.9 (4)	C28—C25—C26—C27	−179.2 (3)
C8—C9—C10—C13	177.9 (2)	C25—C26—C27—C22	−0.4 (4)
C9—C10—C11—C12	2.5 (4)	C23—C22—C27—C26	−0.2 (4)
C13—C10—C11—C12	−177.3 (2)	S1—C22—C27—C26	−178.4 (2)
C10—C11—C12—C7	0.2 (4)	C2—C1—N1—C5	−66.0 (2)
C8—C7—C12—C11	−3.5 (4)	C2—C1—N1—S1	149.75 (17)
C6—C7—C12—C11	178.2 (2)	C4—C5—N1—C1	68.3 (2)
C11—C10—C13—F2	−53.8 (3)	C4—C5—N1—S1	−147.04 (17)
C9—C10—C13—F2	126.4 (3)	C1—N1—S1—O3	−171.68 (17)
C11—C10—C13—F3	−175.3 (2)	C5—N1—S1—O3	46.5 (2)
C9—C10—C13—F3	4.9 (4)	C1—N1—S1—O2	−42.1 (2)
C11—C10—C13—F1	64.7 (3)	C5—N1—S1—O2	176.04 (17)
C9—C10—C13—F1	−115.0 (3)	C1—N1—S1—C22	73.2 (2)
C3—C4—C14—C15	−174.5 (2)	C5—N1—S1—C22	−68.57 (19)
C5—C4—C14—C15	6.6 (4)	C23—C22—S1—O3	157.8 (2)
C4—C14—C15—C20	32.8 (4)	C27—C22—S1—O3	−24.0 (2)
C4—C14—C15—C16	−152.7 (3)	C23—C22—S1—O2	25.9 (2)
C20—C15—C16—C17	0.5 (4)	C27—C22—S1—O2	−155.88 (19)
C14—C15—C16—C17	−174.3 (2)	C23—C22—S1—N1	−88.2 (2)
C15—C16—C17—C18	1.6 (4)	C27—C22—S1—N1	90.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29B···O1	0.99	2.57	3.342 (4)	135
C29—H29A···O2ⁱ	0.99	2.53	3.500 (4)	166
C27—H27···O3ⁱⁱ	0.95	2.48	3.362 (3)	155
C5—H5A···Cl1ⁱⁱⁱ	0.99	2.81	3.776 (3)	166

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

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Synthesis, crystal structures and anti-inflammatory activity of four 3,5-bis­(aryl­idene)-N-benzene­sulfonyl-4-piperidone derivatives

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Synthesis, crystal structures and anti-inflammatory activity of four 3,5-bis(arylidene)-N-benzenesulfonyl-4-piperidone derivatives